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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:20 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0002927

Secondary Accession Numbers

HMDB02927

Metabolite Identification

Common Name

Naringin

Description

Naringin, also known as naringoside or naringin hydrate, is a flavanone-7-O-glycoside between the flavanone naringenin and the disaccharide neohesperidose. Naringin belongs to the flavonoid family. Flavonoids consist of 15 carbon atoms in 3 rings, 2 of which must be benzene rings connected by a 3 carbon chain. Naringin contains the basic flavonoid structure along with one rhamnose and one glucose unit attached to its aglycone portion, called naringenin, at the 7-carbon position. The steric hindrance provided by the two sugar units makes naringin less potent than its aglycone counterpart, naringenin. Naringin is a bitter tasting compound. Naringin is found, on average, in the highest concentration within a few different foods, such as rosemaries, grapefruit/pummelo hybrids, and grapefruits and in a lower concentration in grape wines, pummelo, and beers. Naringin has also been detected, but not quantified in several different foods, such as citrus, limes, herbs and spices, common oregano, and mandarin orange (clementine, tangerine). Both naringin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits. Naringin is the major flavonoid glycoside in grapefruit and gives grapefruit juice its bitter taste. Narinigin exerts a variety of pharmacological effects such as antioxidant activity, blood lipid-lowering, anticarcinogenic activity, and inhibition of selected cytochrome P450 enzymes including CYP3A4 and CYP1A2, which may result in several drug interactions in-vitro.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652305271900232D          

 41 45  0  0  1  0            999 V2000
   21.7678  -13.0650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3420  -13.8956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4965  -16.7748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7614  -11.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2062  -15.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6192  -11.4040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1999  -13.8846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1871  -10.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8721  -16.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8572  -12.6780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0612  -15.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1967  -13.0596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4296  -13.9155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4296  -16.3905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7805  -16.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6256  -13.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0580  -14.3053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.4806  -12.6498    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.7772  -15.5400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.9096  -12.6443    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.7709  -13.8900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.4774  -11.8248    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.4901  -15.1248    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.9063  -11.8193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.4870  -14.2998    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.1903  -11.4096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.7151  -14.3280    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.7151  -15.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4296  -15.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8815  -15.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6291  -14.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.0006  -13.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.5717  -13.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2862  -12.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2862  -14.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0006  -13.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  1  0  0  0
 21  1  1  6  0  0  0
 17  2  1  1  0  0  0
  2 31  1  0  0  0  0
  3 15  1  0  0  0  0
 22  4  1  6  0  0  0
 23  5  1  6  0  0  0
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 26  8  1  6  0  0  0
  9 30  1  0  0  0  0
 10 32  1  0  0  0  0
 11 17  1  0  0  0  0
 11 19  1  0  0  0  0
 12 18  1  0  0  0  0
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 17 21  1  0  0  0  0
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 34 40  2  0  0  0  0
 34 41  1  0  0  0  0
 38 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END

HMDB0002927
     RDKit          3D
Naringin
 73 77  0  0  0  0  0  0  0  0999 V2000
   -3.6432    3.0484    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8651    2.3187    1.5244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3652    1.1083    1.0841 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7094   -0.9007    0.1640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6744   -1.0926   -1.2125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2166   -1.2325   -1.6946 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3993   -0.2578   -1.1816 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7515   -0.5031   -0.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -1.7569   -0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853   -1.9242    0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533   -3.2195    0.8654 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1256   -0.8771    1.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0000    2.5818    1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2226    1.9919   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905    2.1854   -0.9500 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0607    0.9797   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3590   -1.0567    1.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997   -2.1130    1.6534 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9418   -2.1611   -3.6882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7944   -1.5890   -4.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7389   -0.6967   -4.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639   -3.0363   -2.8094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0249   -4.1955   -2.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3056   -2.4182   -1.5811 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7144   -2.2992   -1.6277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4821   -0.0121    1.3990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6086   -0.2840    0.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8731    1.0672    2.3453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0409    1.7368    1.9175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7915    2.0329    2.6856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0800    1.6532    3.8300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8014    4.0863    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0175    3.0557   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    2.5971    0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6586    0.8405   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1536   -0.2322   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0117    0.0407    3.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1716   -2.7886   -4.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3403   -2.4583   -5.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564   -1.1806   -5.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818    0.2504   -4.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6211   -3.4181   -3.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0728   -4.3962   -1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220   -3.0928   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0755   -2.6704   -2.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755   -0.9748    1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2272   -0.8113    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5020    0.8773    4.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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  4  5  1  0
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  7 28  1  0
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  1 42  1  0
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  1 44  1  0
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  4 46  1  6
  6 47  1  6
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 35 67  1  0
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 38 70  1  1
 39 71  1  0
 40 72  1  1
 41 73  1  0
M  END

  Mrv1652305271900232D          

 41 45  0  0  1  0            999 V2000
   21.7678  -13.0650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3420  -13.8956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4965  -16.7748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7614  -11.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2062  -15.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6192  -11.4040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   23.1871  -10.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.8815  -15.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6291  -14.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5717  -13.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1441  -14.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0006  -13.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1441  -15.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6291  -15.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8815  -13.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5717  -13.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2862  -12.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2862  -14.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0006  -13.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  1  0  0  0
 21  1  1  6  0  0  0
 17  2  1  1  0  0  0
  2 31  1  0  0  0  0
  3 15  1  0  0  0  0
 22  4  1  6  0  0  0
 23  5  1  6  0  0  0
 24  6  1  1  0  0  0
 25  7  1  1  0  0  0
 26  8  1  6  0  0  0
  9 30  1  0  0  0  0
 10 32  1  0  0  0  0
 11 17  1  0  0  0  0
 11 19  1  0  0  0  0
 12 18  1  0  0  0  0
 12 20  1  0  0  0  0
 13 27  1  0  0  0  0
 13 33  1  0  0  0  0
 14 29  2  0  0  0  0
 19 15  1  1  0  0  0
 20 16  1  6  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  1  0  0  0  0
 20 24  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 27 28  1  0  0  0  0
 27 34  1  1  0  0  0
 28 29  1  0  0  0  0
 29 35  1  0  0  0  0
 30 35  2  0  0  0  0
 30 36  1  0  0  0  0
 31 36  2  0  0  0  0
 31 37  1  0  0  0  0
 32 38  2  0  0  0  0
 32 39  1  0  0  0  0
 33 35  1  0  0  0  0
 33 37  2  0  0  0  0
 34 40  2  0  0  0  0
 34 41  1  0  0  0  0
 38 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002927

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

> <INCHI_KEY>
DFPMSGMNTNDNHN-ZPHOTFPESA-N

> <FORMULA>
C27H32O14

> <MOLECULAR_WEIGHT>
580.5346

> <EXACT_MASS>
580.179205732

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.192538149282456

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
-0.24

> <JCHEM_LOGP>
-0.15688572199999937

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.530202112756454

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.579343377607254

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121826294490695

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999995

> <JCHEM_REFRACTIVITY>
134.30379999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naringin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002927
     RDKit          3D
Naringin
 73 77  0  0  0  0  0  0  0  0999 V2000
   -3.6432    3.0484    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8651    2.3187    1.5244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3652    1.1083    1.0841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349    0.3141    0.5059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7094   -0.9007    0.1640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6744   -1.0926   -1.2125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2166   -1.2325   -1.6946 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3993   -0.2578   -1.1816 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7515   -0.5031   -0.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -1.7569   -0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853   -1.9242    0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533   -3.2195    0.8654 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1256   -0.8771    1.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6766    0.3921    0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5226    0.5659    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4320    1.4571    1.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5962    1.3647    1.9819 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8295    1.5581    1.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8238    2.3687    1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0000    2.5818    1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2226    1.9919   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905    2.1854   -0.9500 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2314    1.1821   -0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0607    0.9797   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7434    0.0438    2.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3590   -1.0567    1.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997   -2.1130    1.6534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089   -1.1158   -3.0796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9418   -2.1611   -3.6882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7944   -1.5890   -4.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7389   -0.6967   -4.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639   -3.0363   -2.8094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0249   -4.1955   -2.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3056   -2.4182   -1.5811 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7144   -2.2992   -1.6277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4821   -0.0121    1.3990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6086   -0.2840    0.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8731    1.0672    2.3453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0409    1.7368    1.9175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7915    2.0329    2.6856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0800    1.6532    3.8300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8014    4.0863    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0175    3.0557   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    2.5971    0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453    2.9523    1.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586    0.8405   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1536   -0.2322   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968   -2.2647   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342   -2.6612   -0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3278   -4.0266    0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1761    1.5601   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5320    2.1633    2.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7388    2.8714    2.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917    3.2158    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1021    2.7819   -0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3483    0.6937   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998    0.3394   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7728   -0.0199    3.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0117    0.0407    3.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1716   -2.7886   -4.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3403   -2.4583   -5.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564   -1.1806   -5.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818    0.2504   -4.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6211   -3.4181   -3.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0728   -4.3962   -1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220   -3.0928   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0755   -2.6704   -2.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755   -0.9748    1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2272   -0.8113    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1825    0.5669    3.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6745    1.8818    2.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    3.0122    2.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5020    0.8773    4.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 17 25  1  0
 25 26  1  0
 26 27  2  0
  7 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 29 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
  4 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 40  2  1  0
 34  6  1  0
 15  9  1  0
 24 18  1  0
 26 13  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  1
  4 46  1  6
  6 47  1  6
  7 48  1  6
 10 49  1  0
 12 50  1  0
 15 51  1  0
 17 52  1  1
 19 53  1  0
 20 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 29 60  1  6
 30 61  1  0
 30 62  1  0
 31 63  1  0
 32 64  1  6
 33 65  1  0
 34 66  1  1
 35 67  1  0
 36 68  1  1
 37 69  1  0
 38 70  1  1
 39 71  1  0
 40 72  1  1
 41 73  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      40.633 -24.388   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      37.972 -25.938   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      41.993 -31.313   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      40.621 -21.308   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      43.318 -28.998   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      45.956 -21.287   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      43.306 -25.918   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      43.283 -19.758   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      35.228 -30.649   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      25.867 -23.666   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      39.314 -28.243   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      43.301 -24.378   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      32.535 -25.976   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      32.535 -30.596   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      40.657 -30.548   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.968 -24.367   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      39.308 -26.703   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.964 -23.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      40.651 -29.008   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.631 -23.603   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      40.639 -25.928   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      41.958 -22.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      41.982 -28.233   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      44.625 -22.063   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      41.976 -26.693   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      43.289 -21.298   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      31.202 -26.746   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      31.202 -28.286   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      32.535 -29.056   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      35.245 -29.109   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      36.641 -26.714   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      27.201 -24.436   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      33.869 -26.746   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      29.868 -25.976   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      33.869 -28.286   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      36.641 -28.318   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      35.245 -25.922   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      27.201 -25.976   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      28.534 -23.666   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      28.534 -26.746   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      29.868 -24.436   0.000  0.00  0.00           C+0
CONECT    1   18   21                                                       
CONECT    2   17   31                                                       
CONECT    3   15                                                            
CONECT    4   22                                                            
CONECT    5   23                                                            
CONECT    6   24                                                            
CONECT    7   25                                                            
CONECT    8   26                                                            
CONECT    9   30                                                            
CONECT   10   32                                                            
CONECT   11   17   19                                                       
CONECT   12   18   20                                                       
CONECT   13   27   33                                                       
CONECT   14   29                                                            
CONECT   15    3   19                                                       
CONECT   16   20                                                            
CONECT   17    2   11   21                                                  
CONECT   18    1   12   22                                                  
CONECT   19   11   15   23                                                  
CONECT   20   12   16   24                                                  
CONECT   21    1   17   25                                                  
CONECT   22    4   18   26                                                  
CONECT   23    5   19   25                                                  
CONECT   24    6   20   26                                                  
CONECT   25    7   21   23                                                  
CONECT   26    8   22   24                                                  
CONECT   27   13   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   14   28   35                                                  
CONECT   30    9   35   36                                                  
CONECT   31    2   36   37                                                  
CONECT   32   10   38   39                                                  
CONECT   33   13   35   37                                                  
CONECT   34   27   40   41                                                  
CONECT   35   29   30   33                                                  
CONECT   36   30   31                                                       
CONECT   37   31   33                                                       
CONECT   38   32   40                                                       
CONECT   39   32   41                                                       
CONECT   40   34   38                                                       
CONECT   41   34   39                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

COMPND    HMDB0002927
HETATM    1  C1  UNL     1      -3.643   3.048   0.457  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.865   2.319   1.524  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.365   1.108   1.084  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.335   0.314   0.506  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.709  -0.901   0.164  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.674  -1.093  -1.213  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.217  -1.232  -1.695  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.399  -0.258  -1.182  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.752  -0.503  -0.458  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.229  -1.757  -0.157  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.385  -1.924   0.570  1.00  0.00           C  
HETATM   12  O4  UNL     1       2.853  -3.219   0.865  1.00  0.00           O  
HETATM   13  C9  UNL     1       3.126  -0.877   1.034  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.677   0.392   0.751  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.523   0.566   0.025  1.00  0.00           C  
HETATM   16  O5  UNL     1       3.432   1.457   1.224  1.00  0.00           O  
HETATM   17  C12 UNL     1       4.596   1.365   1.982  1.00  0.00           C  
HETATM   18  C13 UNL     1       5.829   1.558   1.197  1.00  0.00           C  
HETATM   19  C14 UNL     1       6.824   2.369   1.705  1.00  0.00           C  
HETATM   20  C15 UNL     1       8.000   2.582   1.006  1.00  0.00           C  
HETATM   21  C16 UNL     1       8.223   1.992  -0.224  1.00  0.00           C  
HETATM   22  O6  UNL     1       9.391   2.185  -0.950  1.00  0.00           O  
HETATM   23  C17 UNL     1       7.231   1.182  -0.733  1.00  0.00           C  
HETATM   24  C18 UNL     1       6.061   0.980  -0.021  1.00  0.00           C  
HETATM   25  C19 UNL     1       4.743   0.044   2.722  1.00  0.00           C  
HETATM   26  C20 UNL     1       4.359  -1.057   1.809  1.00  0.00           C  
HETATM   27  O7  UNL     1       5.000  -2.113   1.653  1.00  0.00           O  
HETATM   28  O8  UNL     1      -1.309  -1.116  -3.080  1.00  0.00           O  
HETATM   29  C21 UNL     1      -1.942  -2.161  -3.688  1.00  0.00           C  
HETATM   30  C22 UNL     1      -2.794  -1.589  -4.820  1.00  0.00           C  
HETATM   31  O9  UNL     1      -3.739  -0.697  -4.368  1.00  0.00           O  
HETATM   32  C23 UNL     1      -2.764  -3.036  -2.809  1.00  0.00           C  
HETATM   33  O10 UNL     1      -2.025  -4.195  -2.474  1.00  0.00           O  
HETATM   34  C24 UNL     1      -3.306  -2.418  -1.581  1.00  0.00           C  
HETATM   35  O11 UNL     1      -4.714  -2.299  -1.628  1.00  0.00           O  
HETATM   36  C25 UNL     1      -4.482  -0.012   1.399  1.00  0.00           C  
HETATM   37  O12 UNL     1      -5.609  -0.284   0.588  1.00  0.00           O  
HETATM   38  C26 UNL     1      -4.873   1.067   2.345  1.00  0.00           C  
HETATM   39  O13 UNL     1      -6.041   1.737   1.918  1.00  0.00           O  
HETATM   40  C27 UNL     1      -3.791   2.033   2.686  1.00  0.00           C  
HETATM   41  O14 UNL     1      -3.080   1.653   3.830  1.00  0.00           O  
HETATM   42  H1  UNL     1      -3.801   4.086   0.762  1.00  0.00           H  
HETATM   43  H2  UNL     1      -3.018   3.056  -0.464  1.00  0.00           H  
HETATM   44  H3  UNL     1      -4.630   2.597   0.263  1.00  0.00           H  
HETATM   45  H4  UNL     1      -2.045   2.952   1.876  1.00  0.00           H  
HETATM   46  H5  UNL     1      -3.659   0.840  -0.436  1.00  0.00           H  
HETATM   47  H6  UNL     1      -3.154  -0.232  -1.722  1.00  0.00           H  
HETATM   48  H7  UNL     1      -0.897  -2.265  -1.495  1.00  0.00           H  
HETATM   49  H8  UNL     1       0.734  -2.661  -0.467  1.00  0.00           H  
HETATM   50  H9  UNL     1       2.328  -4.027   0.535  1.00  0.00           H  
HETATM   51  H10 UNL     1       1.176   1.560  -0.194  1.00  0.00           H  
HETATM   52  H11 UNL     1       4.532   2.163   2.770  1.00  0.00           H  
HETATM   53  H12 UNL     1       6.739   2.871   2.658  1.00  0.00           H  
HETATM   54  H13 UNL     1       8.792   3.216   1.390  1.00  0.00           H  
HETATM   55  H14 UNL     1      10.102   2.782  -0.558  1.00  0.00           H  
HETATM   56  H15 UNL     1       7.348   0.694  -1.690  1.00  0.00           H  
HETATM   57  H16 UNL     1       5.300   0.339  -0.444  1.00  0.00           H  
HETATM   58  H17 UNL     1       5.773  -0.020   3.074  1.00  0.00           H  
HETATM   59  H18 UNL     1       4.012   0.041   3.567  1.00  0.00           H  
HETATM   60  H19 UNL     1      -1.172  -2.789  -4.188  1.00  0.00           H  
HETATM   61  H20 UNL     1      -3.340  -2.458  -5.262  1.00  0.00           H  
HETATM   62  H21 UNL     1      -2.156  -1.181  -5.632  1.00  0.00           H  
HETATM   63  H22 UNL     1      -3.482   0.250  -4.459  1.00  0.00           H  
HETATM   64  H23 UNL     1      -3.621  -3.418  -3.417  1.00  0.00           H  
HETATM   65  H24 UNL     1      -2.073  -4.396  -1.521  1.00  0.00           H  
HETATM   66  H25 UNL     1      -3.122  -3.093  -0.693  1.00  0.00           H  
HETATM   67  H26 UNL     1      -5.075  -2.670  -2.472  1.00  0.00           H  
HETATM   68  H27 UNL     1      -4.275  -0.975   1.936  1.00  0.00           H  
HETATM   69  H28 UNL     1      -6.227  -0.811   1.155  1.00  0.00           H  
HETATM   70  H29 UNL     1      -5.182   0.567   3.309  1.00  0.00           H  
HETATM   71  H30 UNL     1      -6.674   1.882   2.640  1.00  0.00           H  
HETATM   72  H31 UNL     1      -4.284   3.012   2.944  1.00  0.00           H  
HETATM   73  H32 UNL     1      -3.502   0.877   4.271  1.00  0.00           H  
CONECT    1    2   42   43   44
CONECT    2    3   40   45
CONECT    3    4
CONECT    4    5   36   46
CONECT    5    6
CONECT    6    7   34   47
CONECT    7    8   28   48
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   49
CONECT   11   12   13   13
CONECT   12   50
CONECT   13   14   26
CONECT   14   15   15   16
CONECT   15   51
CONECT   16   17
CONECT   17   18   25   52
CONECT   18   19   19   24
CONECT   19   20   53
CONECT   20   21   21   54
CONECT   21   22   23
CONECT   22   55
CONECT   23   24   24   56
CONECT   24   57
CONECT   25   26   58   59
CONECT   26   27   27
CONECT   28   29
CONECT   29   30   32   60
CONECT   30   31   61   62
CONECT   31   63
CONECT   32   33   34   64
CONECT   33   65
CONECT   34   35   66
CONECT   35   67
CONECT   36   37   38   68
CONECT   37   69
CONECT   38   39   40   70
CONECT   39   71
CONECT   40   41   72
CONECT   41   73
END

HMDB0002927
     RDKit          3D
Naringin
 73 77  0  0  0  0  0  0  0  0999 V2000
   -3.6432    3.0484    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8651    2.3187    1.5244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3652    1.1083    1.0841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349    0.3141    0.5059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7094   -0.9007    0.1640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6744   -1.0926   -1.2125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2166   -1.2325   -1.6946 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3993   -0.2578   -1.1816 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7515   -0.5031   -0.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -1.7569   -0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853   -1.9242    0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533   -3.2195    0.8654 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1256   -0.8771    1.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6766    0.3921    0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5226    0.5659    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4320    1.4571    1.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5962    1.3647    1.9819 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8295    1.5581    1.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8238    2.3687    1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0000    2.5818    1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2226    1.9919   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905    2.1854   -0.9500 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2314    1.1821   -0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0607    0.9797   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7434    0.0438    2.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3590   -1.0567    1.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997   -2.1130    1.6534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089   -1.1158   -3.0796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9418   -2.1611   -3.6882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7944   -1.5890   -4.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7389   -0.6967   -4.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639   -3.0363   -2.8094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0249   -4.1955   -2.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3056   -2.4182   -1.5811 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7144   -2.2992   -1.6277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4821   -0.0121    1.3990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6086   -0.2840    0.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8731    1.0672    2.3453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0409    1.7368    1.9175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7915    2.0329    2.6856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0800    1.6532    3.8300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8014    4.0863    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0175    3.0557   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    2.5971    0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453    2.9523    1.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586    0.8405   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1536   -0.2322   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968   -2.2647   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342   -2.6612   -0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3278   -4.0266    0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1761    1.5601   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5320    2.1633    2.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7388    2.8714    2.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917    3.2158    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1021    2.7819   -0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3483    0.6937   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998    0.3394   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7728   -0.0199    3.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0117    0.0407    3.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1716   -2.7886   -4.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3403   -2.4583   -5.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564   -1.1806   -5.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818    0.2504   -4.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6211   -3.4181   -3.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0728   -4.3962   -1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220   -3.0928   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0755   -2.6704   -2.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755   -0.9748    1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2272   -0.8113    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1825    0.5669    3.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6745    1.8818    2.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    3.0122    2.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5020    0.8773    4.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 17 25  1  0
 25 26  1  0
 26 27  2  0
  7 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 29 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
  4 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 40  2  1  0
 34  6  1  0
 15  9  1  0
 24 18  1  0
 26 13  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  1
  4 46  1  6
  6 47  1  6
  7 48  1  6
 10 49  1  0
 12 50  1  0
 15 51  1  0
 17 52  1  1
 19 53  1  0
 20 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 29 60  1  6
 30 61  1  0
 30 62  1  0
 31 63  1  0
 32 64  1  6
 33 65  1  0
 34 66  1  1
 35 67  1  0
 36 68  1  1
 37 69  1  0
 38 70  1  1
 39 71  1  0
 40 72  1  1
 41 73  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]	ChEBI
Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucoside	ChEBI
Naringenin 7-O-neohesperidoside	ChEBI
Naringoside	ChEBI
Naringenin 7-O-[a-L-rhamnosyl-(1->2)-b-D-glucoside]	Generator
Naringenin 7-O-[α-L-rhamnosyl-(1->2)-β-D-glucoside]	Generator
Naringenin 7-O-a-L-rhamnosyl-(1->2)-b-D-glucoside	Generator
Naringenin 7-O-α-L-rhamnosyl-(1->2)-β-D-glucoside	Generator
4',5,7-Trihydroxyflavanone 7-rhamnoglucoside	MeSH
Cyclorel	MeSH
Aurantiin	MeSH
Naringenin-7-hesperidoside	MeSH
Naringin dihydrochalcone	MeSH
Naringin sodium	MeSH
4'5-DiOH-flavone-7-rhgluc	HMDB
Naringin hydrate	HMDB
Nobiletin	HMDB

Chemical Formula

C₂₇H₃₂O₁₄

Average Molecular Weight

580.5346

Monoisotopic Molecular Weight

580.179205732

IUPAC Name

(2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

naringin

CAS Registry Number

10236-47-2

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

InChI Key

DFPMSGMNTNDNHN-ZPHOTFPESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Oxane
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

disaccharide derivative (CHEBI:28819 )
dihydroxyflavanone (CHEBI:28819 )
neohesperidoside (CHEBI:28819 )
flavanones (C09789 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Fibroblast (HMDB: HMDB0002927)

Fibroblasts (HMDB: HMDB0002927)

Tissue

Epithelium

Epidermis (HMDB: HMDB0002927)

Excreta

Biofluid or Excreta

Urine (PMID: 10637051)

Cellular substructure

Cytoplasm (HMDB: HMDB0002927)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002927)

Source

Exogenous

Exogenous (HMDB: HMDB0002927)

Food

Food (HMDB: HMDB0002927)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Other beverage

Fruit juice (FooDB: FOOD00763)

Fruit

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)
Sour orange (FooDB: FOOD00918)

Tropical fruit

Kumquat (FooDB: FOOD00393)
Pomegranate (FooDB: FOOD00151)

Fruits (FooDB: FOOD00871)

Herb and spice

Herb

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0002927)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	83 °C	Not Available
Boiling Point	922.00 to 926.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1 mg/mL at 40 °C	Not Available
LogP	-0.44	PERRISSOUD,D & TESTA,B (1986)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	217.329	30932474
[M+H]+	Baker	240.62	30932474
[M+H]+	MetCCS_train_pos	237.453	30932474
[M-H]-	Not Available	217.329	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000543
[M+H]+	Not Available	239.5	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000543

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.06 g/L	ALOGPS
logP	-0.24	ALOGPS
logP	-0.16	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	134.3 m³·mol⁻¹	ChemAxon
Polarizability	56.19 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	227.154	30932474
DeepCCS	[M-H]-	225.225	30932474
DeepCCS	[M-2H]-	259.039	30932474
DeepCCS	[M+Na]+	233.225	30932474
AllCCS	[M+H]+	228.5	32859911
AllCCS	[M+H-H2O]+	227.3	32859911
AllCCS	[M+NH4]+	229.6	32859911
AllCCS	[M+Na]+	229.9	32859911
AllCCS	[M-H]-	222.3	32859911
AllCCS	[M+Na-2H]-	224.3	32859911
AllCCS	[M+HCOO]-	226.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Naringin	C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O	5296.7	Standard polar	33892256
Naringin	C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O	4704.0	Standard non polar	33892256
Naringin	C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O	5202.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Naringin,1TMS,isomer #1	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4747.1	Semi standard non polar	33892256
Naringin,1TMS,isomer #2	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4757.2	Semi standard non polar	33892256
Naringin,1TMS,isomer #3	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4766.9	Semi standard non polar	33892256
Naringin,1TMS,isomer #4	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4762.6	Semi standard non polar	33892256
Naringin,1TMS,isomer #5	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4821.9	Semi standard non polar	33892256
Naringin,1TMS,isomer #6	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4754.3	Semi standard non polar	33892256
Naringin,1TMS,isomer #7	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4748.7	Semi standard non polar	33892256
Naringin,1TMS,isomer #8	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4772.6	Semi standard non polar	33892256
Naringin,2TMS,isomer #1	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4635.8	Semi standard non polar	33892256
Naringin,2TMS,isomer #10	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4667.1	Semi standard non polar	33892256
Naringin,2TMS,isomer #11	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4622.2	Semi standard non polar	33892256
Naringin,2TMS,isomer #12	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4611.0	Semi standard non polar	33892256
Naringin,2TMS,isomer #13	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4637.0	Semi standard non polar	33892256
Naringin,2TMS,isomer #14	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4665.3	Semi standard non polar	33892256
Naringin,2TMS,isomer #15	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4727.0	Semi standard non polar	33892256
Naringin,2TMS,isomer #16	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4644.9	Semi standard non polar	33892256
Naringin,2TMS,isomer #17	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4634.5	Semi standard non polar	33892256
Naringin,2TMS,isomer #18	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4662.4	Semi standard non polar	33892256
Naringin,2TMS,isomer #19	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4731.5	Semi standard non polar	33892256
Naringin,2TMS,isomer #2	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4699.8	Semi standard non polar	33892256
Naringin,2TMS,isomer #20	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4636.6	Semi standard non polar	33892256
Naringin,2TMS,isomer #21	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4627.9	Semi standard non polar	33892256
Naringin,2TMS,isomer #22	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4661.4	Semi standard non polar	33892256
Naringin,2TMS,isomer #23	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4709.2	Semi standard non polar	33892256
Naringin,2TMS,isomer #24	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4698.9	Semi standard non polar	33892256
Naringin,2TMS,isomer #25	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4726.8	Semi standard non polar	33892256
Naringin,2TMS,isomer #26	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4639.7	Semi standard non polar	33892256
Naringin,2TMS,isomer #27	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4638.0	Semi standard non polar	33892256
Naringin,2TMS,isomer #28	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4649.1	Semi standard non polar	33892256
Naringin,2TMS,isomer #3	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4635.7	Semi standard non polar	33892256
Naringin,2TMS,isomer #4	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4646.3	Semi standard non polar	33892256
Naringin,2TMS,isomer #5	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4620.5	Semi standard non polar	33892256
Naringin,2TMS,isomer #6	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4597.5	Semi standard non polar	33892256
Naringin,2TMS,isomer #7	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4624.5	Semi standard non polar	33892256
Naringin,2TMS,isomer #8	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4645.6	Semi standard non polar	33892256
Naringin,2TMS,isomer #9	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4708.4	Semi standard non polar	33892256
Naringin,3TMS,isomer #1	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4587.4	Semi standard non polar	33892256
Naringin,3TMS,isomer #10	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4556.9	Semi standard non polar	33892256
Naringin,3TMS,isomer #11	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4581.5	Semi standard non polar	33892256
Naringin,3TMS,isomer #12	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4590.8	Semi standard non polar	33892256
Naringin,3TMS,isomer #13	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4534.6	Semi standard non polar	33892256
Naringin,3TMS,isomer #14	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4510.4	Semi standard non polar	33892256
Naringin,3TMS,isomer #15	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4546.6	Semi standard non polar	33892256
Naringin,3TMS,isomer #16	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4537.5	Semi standard non polar	33892256
Naringin,3TMS,isomer #17	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4510.7	Semi standard non polar	33892256
Naringin,3TMS,isomer #18	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4546.1	Semi standard non polar	33892256
Naringin,3TMS,isomer #19	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4525.2	Semi standard non polar	33892256
Naringin,3TMS,isomer #2	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4545.1	Semi standard non polar	33892256
Naringin,3TMS,isomer #20	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4520.6	Semi standard non polar	33892256
Naringin,3TMS,isomer #21	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4522.7	Semi standard non polar	33892256
Naringin,3TMS,isomer #22	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4590.8	Semi standard non polar	33892256
Naringin,3TMS,isomer #23	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4567.9	Semi standard non polar	33892256
Naringin,3TMS,isomer #24	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4526.7	Semi standard non polar	33892256
Naringin,3TMS,isomer #25	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4511.9	Semi standard non polar	33892256
Naringin,3TMS,isomer #26	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4545.7	Semi standard non polar	33892256
Naringin,3TMS,isomer #27	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4620.3	Semi standard non polar	33892256
Naringin,3TMS,isomer #28	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4573.9	Semi standard non polar	33892256
Naringin,3TMS,isomer #29	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4564.8	Semi standard non polar	33892256
Naringin,3TMS,isomer #3	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4551.2	Semi standard non polar	33892256
Naringin,3TMS,isomer #30	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4589.2	Semi standard non polar	33892256
Naringin,3TMS,isomer #31	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4563.1	Semi standard non polar	33892256
Naringin,3TMS,isomer #32	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4544.9	Semi standard non polar	33892256
Naringin,3TMS,isomer #33	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4574.5	Semi standard non polar	33892256
Naringin,3TMS,isomer #34	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4527.1	Semi standard non polar	33892256
Naringin,3TMS,isomer #35	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4523.8	Semi standard non polar	33892256
Naringin,3TMS,isomer #36	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4527.3	Semi standard non polar	33892256
Naringin,3TMS,isomer #37	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4608.1	Semi standard non polar	33892256
Naringin,3TMS,isomer #38	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4552.3	Semi standard non polar	33892256
Naringin,3TMS,isomer #39	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4539.6	Semi standard non polar	33892256
Naringin,3TMS,isomer #4	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4527.8	Semi standard non polar	33892256
Naringin,3TMS,isomer #40	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4571.5	Semi standard non polar	33892256
Naringin,3TMS,isomer #41	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4591.0	Semi standard non polar	33892256
Naringin,3TMS,isomer #42	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4582.4	Semi standard non polar	33892256
Naringin,3TMS,isomer #43	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4608.4	Semi standard non polar	33892256
Naringin,3TMS,isomer #44	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4561.4	Semi standard non polar	33892256
Naringin,3TMS,isomer #45	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4558.0	Semi standard non polar	33892256
Naringin,3TMS,isomer #46	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4563.5	Semi standard non polar	33892256
Naringin,3TMS,isomer #47	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4596.1	Semi standard non polar	33892256
Naringin,3TMS,isomer #48	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4584.5	Semi standard non polar	33892256
Naringin,3TMS,isomer #49	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4610.0	Semi standard non polar	33892256
Naringin,3TMS,isomer #5	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4505.5	Semi standard non polar	33892256
Naringin,3TMS,isomer #50	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4548.5	Semi standard non polar	33892256
Naringin,3TMS,isomer #51	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4543.0	Semi standard non polar	33892256
Naringin,3TMS,isomer #52	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4550.1	Semi standard non polar	33892256
Naringin,3TMS,isomer #53	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4593.3	Semi standard non polar	33892256
Naringin,3TMS,isomer #54	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4586.3	Semi standard non polar	33892256
Naringin,3TMS,isomer #55	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4590.6	Semi standard non polar	33892256
Naringin,3TMS,isomer #56	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4561.2	Semi standard non polar	33892256
Naringin,3TMS,isomer #6	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4538.2	Semi standard non polar	33892256
Naringin,3TMS,isomer #7	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4584.8	Semi standard non polar	33892256
Naringin,3TMS,isomer #8	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4589.6	Semi standard non polar	33892256
Naringin,3TMS,isomer #9	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4570.3	Semi standard non polar	33892256
Naringin,4TMS,isomer #1	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4507.5	Semi standard non polar	33892256
Naringin,4TMS,isomer #10	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4442.5	Semi standard non polar	33892256
Naringin,4TMS,isomer #11	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4422.1	Semi standard non polar	33892256
Naringin,4TMS,isomer #12	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4449.8	Semi standard non polar	33892256
Naringin,4TMS,isomer #13	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4430.5	Semi standard non polar	33892256
Naringin,4TMS,isomer #14	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4411.7	Semi standard non polar	33892256
Naringin,4TMS,isomer #15	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4427.7	Semi standard non polar	33892256
Naringin,4TMS,isomer #16	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4546.5	Semi standard non polar	33892256
Naringin,4TMS,isomer #17	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4499.6	Semi standard non polar	33892256
Naringin,4TMS,isomer #18	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4492.7	Semi standard non polar	33892256
Naringin,4TMS,isomer #19	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4515.1	Semi standard non polar	33892256
Naringin,4TMS,isomer #2	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4507.5	Semi standard non polar	33892256
Naringin,4TMS,isomer #20	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4495.3	Semi standard non polar	33892256
Naringin,4TMS,isomer #21	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4486.4	Semi standard non polar	33892256
Naringin,4TMS,isomer #22	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4505.3	Semi standard non polar	33892256
Naringin,4TMS,isomer #23	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4496.2	Semi standard non polar	33892256
Naringin,4TMS,isomer #24	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4483.1	Semi standard non polar	33892256
Naringin,4TMS,isomer #25	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4498.0	Semi standard non polar	33892256
Naringin,4TMS,isomer #26	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4490.7	Semi standard non polar	33892256
Naringin,4TMS,isomer #27	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4469.6	Semi standard non polar	33892256
Naringin,4TMS,isomer #28	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4503.1	Semi standard non polar	33892256
Naringin,4TMS,isomer #29	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4449.0	Semi standard non polar	33892256
Naringin,4TMS,isomer #3	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4495.2	Semi standard non polar	33892256
Naringin,4TMS,isomer #30	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4433.3	Semi standard non polar	33892256
Naringin,4TMS,isomer #31	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4453.0	Semi standard non polar	33892256
Naringin,4TMS,isomer #32	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4442.8	Semi standard non polar	33892256
Naringin,4TMS,isomer #33	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4427.7	Semi standard non polar	33892256
Naringin,4TMS,isomer #34	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4446.1	Semi standard non polar	33892256
Naringin,4TMS,isomer #35	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4436.0	Semi standard non polar	33892256
Naringin,4TMS,isomer #36	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4526.2	Semi standard non polar	33892256
Naringin,4TMS,isomer #37	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4499.9	Semi standard non polar	33892256
Naringin,4TMS,isomer #38	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4500.1	Semi standard non polar	33892256
Naringin,4TMS,isomer #39	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4516.8	Semi standard non polar	33892256
Naringin,4TMS,isomer #4	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4495.4	Semi standard non polar	33892256
Naringin,4TMS,isomer #40	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4468.3	Semi standard non polar	33892256
Naringin,4TMS,isomer #41	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4448.7	Semi standard non polar	33892256
Naringin,4TMS,isomer #42	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4480.7	Semi standard non polar	33892256
Naringin,4TMS,isomer #43	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4432.8	Semi standard non polar	33892256
Naringin,4TMS,isomer #44	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4419.8	Semi standard non polar	33892256
Naringin,4TMS,isomer #45	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4434.5	Semi standard non polar	33892256
Naringin,4TMS,isomer #46	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4526.6	Semi standard non polar	33892256
Naringin,4TMS,isomer #47	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4517.3	Semi standard non polar	33892256
Naringin,4TMS,isomer #48	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4541.2	Semi standard non polar	33892256
Naringin,4TMS,isomer #49	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4498.1	Semi standard non polar	33892256
Naringin,4TMS,isomer #5	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4512.4	Semi standard non polar	33892256
Naringin,4TMS,isomer #50	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4493.6	Semi standard non polar	33892256
Naringin,4TMS,isomer #51	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4499.6	Semi standard non polar	33892256
Naringin,4TMS,isomer #52	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4473.3	Semi standard non polar	33892256
Naringin,4TMS,isomer #53	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4461.8	Semi standard non polar	33892256
Naringin,4TMS,isomer #54	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4477.0	Semi standard non polar	33892256
Naringin,4TMS,isomer #55	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4447.0	Semi standard non polar	33892256
Naringin,4TMS,isomer #56	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4510.9	Semi standard non polar	33892256
Naringin,4TMS,isomer #57	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4504.8	Semi standard non polar	33892256
Naringin,4TMS,isomer #58	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4525.3	Semi standard non polar	33892256
Naringin,4TMS,isomer #59	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4477.0	Semi standard non polar	33892256
Naringin,4TMS,isomer #6	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4500.3	Semi standard non polar	33892256
Naringin,4TMS,isomer #60	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4458.3	Semi standard non polar	33892256
Naringin,4TMS,isomer #61	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4475.8	Semi standard non polar	33892256
Naringin,4TMS,isomer #62	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4517.8	Semi standard non polar	33892256
Naringin,4TMS,isomer #63	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4509.9	Semi standard non polar	33892256
Naringin,4TMS,isomer #64	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4520.5	Semi standard non polar	33892256
Naringin,4TMS,isomer #65	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4491.7	Semi standard non polar	33892256
Naringin,4TMS,isomer #66	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	4514.5	Semi standard non polar	33892256
Naringin,4TMS,isomer #67	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	4506.9	Semi standard non polar	33892256
Naringin,4TMS,isomer #68	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4515.7	Semi standard non polar	33892256
Naringin,4TMS,isomer #69	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4464.7	Semi standard non polar	33892256
Naringin,4TMS,isomer #7	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	4451.6	Semi standard non polar	33892256
Naringin,4TMS,isomer #70	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4509.4	Semi standard non polar	33892256
Naringin,4TMS,isomer #8	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	4431.7	Semi standard non polar	33892256
Naringin,4TMS,isomer #9	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	4460.9	Semi standard non polar	33892256
Naringin,1TBDMS,isomer #1	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O	4976.5	Semi standard non polar	33892256
Naringin,1TBDMS,isomer #2	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	4985.1	Semi standard non polar	33892256
Naringin,1TBDMS,isomer #3	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	5007.7	Semi standard non polar	33892256
Naringin,1TBDMS,isomer #4	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	5008.0	Semi standard non polar	33892256
Naringin,1TBDMS,isomer #5	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	5069.1	Semi standard non polar	33892256
Naringin,1TBDMS,isomer #6	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	4988.3	Semi standard non polar	33892256
Naringin,1TBDMS,isomer #7	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4991.2	Semi standard non polar	33892256
Naringin,1TBDMS,isomer #8	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	5009.7	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #1	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O	5072.3	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #10	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	5088.2	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #11	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	5062.3	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #12	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	5056.9	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #13	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	5077.5	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #14	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	5092.9	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #15	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	5149.7	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #16	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	5084.0	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #17	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	5081.2	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #18	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	5103.3	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #19	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	5159.1	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #2	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O	5131.4	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #20	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	5083.9	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #21	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	5087.1	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #22	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	5107.7	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #23	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	5149.0	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #24	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	5148.8	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #25	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	5168.7	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #26	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	5076.7	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #27	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	5084.4	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #28	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	5088.9	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #3	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O	5074.3	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #4	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O	5061.0	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #5	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	5067.7	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #6	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	5053.7	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #7	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	5073.2	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #8	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	5071.2	Semi standard non polar	33892256
Naringin,2TBDMS,isomer #9	C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O	5137.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Naringin GC-EI-TOF (Non-derivatized)	splash10-014j-0920000000-350bda4f263e4440e76a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Naringin GC-EI-TOF (Non-derivatized)	splash10-014j-0920000000-350bda4f263e4440e76a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (Non-derivatized) - 70eV, Positive	splash10-044j-9521280000-3e3e40b7d28b4e903216	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (1 TMS) - 70eV, Positive	splash10-00ei-9302015000-e97b650a0d6a1b78ddc3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS ("Naringin,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_1_8) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naringin GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-001i-0000090000-62ab85e8b85e9515ddc1	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin LC-ESI-ITTOF (Shimadzu LC20A-IT-TOFMS) , Negative-QTOF	splash10-004i-0000091000-2671e4ecb91933035e78	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin ESI-TOF 10V, Negative-QTOF	splash10-004i-0100090000-0c16a31fd116a04809ff	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin ESI-TOF 40V, Negative-QTOF	splash10-00di-0290110000-a72cef11c1816469a269	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin ESI-TOF 10V, Negative-QTOF	splash10-00di-0290110000-a72cef11c1816469a269	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin ESI-TOF 20V, Negative-QTOF	splash10-004i-0000090000-d6285c4e4374990ed161	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin ESI-TOF 30V, Negative-QTOF	splash10-004i-0030290000-06238e4a98a4daad3265	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin ESI-TOF 50V, Negative-QTOF	splash10-004i-0030290000-06238e4a98a4daad3265	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin ESI-TOF 10V, Negative-QTOF	splash10-004i-0100090000-0c16a31fd116a04809ff	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin ESI-TOF 40V, Negative-QTOF	splash10-00di-0290110000-a72cef11c1816469a269	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin ESI-TOF 10V, Negative-QTOF	splash10-004i-0000090000-4498c4e102c3c7d3d514	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin ESI-TOF 20V, Negative-QTOF	splash10-004i-0000090000-d6285c4e4374990ed161	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin ESI-TOF 30V, Negative-QTOF	splash10-004i-0030290000-06238e4a98a4daad3265	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin ESI-TOF 50V, Negative-QTOF	splash10-0fk9-0690000000-3d8f024f57318d3dbca8	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin LC-ESI-qTof , Positive-QTOF	splash10-0fk9-2981000000-e103705338e8e8855307	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin LC-ESI-TOF , negative-QTOF	splash10-00di-0290110000-a72cef11c1816469a269	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin LC-ESI-TOF , negative-QTOF	splash10-004i-0000090000-4498c4e102c3c7d3d514	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin LC-ESI-TOF , negative-QTOF	splash10-004i-0000090000-d6285c4e4374990ed161	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naringin LC-ESI-TOF , negative-QTOF	splash10-004i-0030290000-06238e4a98a4daad3265	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringin 10V, Positive-QTOF	splash10-00xr-0390740000-ed6375341eb1bebac319	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringin 20V, Positive-QTOF	splash10-05fr-0490200000-bbf5e62f8ba5ef5c55c6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringin 40V, Positive-QTOF	splash10-01b9-0940000000-043fddfc9269db83e1f1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringin 10V, Negative-QTOF	splash10-02or-3592880000-a3ec8e8504154578e09f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringin 20V, Negative-QTOF	splash10-0229-2691310000-865585e62bd05144335b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringin 40V, Negative-QTOF	splash10-00di-7590000000-82ba5c0120e07b81e87b	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Epidermis
Fibroblasts

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 208	10637051	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Naringin

METLIN ID

3604

PubChem Compound

442428

PDB ID

Not Available

ChEBI ID

28819

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1400021

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A: Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol. 2003 Jun 15;65(12):2065-71. [PubMed:12787887 ]
Ishii K, Furuta T, Kasuya Y: Determination of naringin and naringenin in human plasma by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Aug 30;683(2):225-9. [PubMed:8891919 ]
Fuhr U, Kummert AL: The fate of naringin in humans: a key to grapefruit juice-drug interactions? Clin Pharmacol Ther. 1995 Oct;58(4):365-73. [PubMed:7586927 ]
Tanaka S, Sato T, Akimoto N, Yano M, Ito A: Prevention of UVB-induced photoinflammation and photoaging by a polymethoxy flavonoid, nobiletin, in human keratinocytes in vivo and in vitro. Biochem Pharmacol. 2004 Aug 1;68(3):433-9. [PubMed:15242810 ]
Zhang J, Brodbelt JS: Screening flavonoid metabolites of naringin and narirutin in urine after human consumption of grapefruit juice by LC-MS and LC-MS/MS. Analyst. 2004 Dec;129(12):1227-33. Epub 2004 Oct 26. [PubMed:15565223 ]
Minagawa A, Otani Y, Kubota T, Wada N, Furukawa T, Kumai K, Kameyama K, Okada Y, Fujii M, Yano M, Sato T, Ito A, Kitajima M: The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice. Jpn J Cancer Res. 2001 Dec;92(12):1322-8. [PubMed:11749698 ]
Ishii K, Furuta T, Kasuya Y: Mass spectrometric identification and high-performance liquid chromatographic determination of a flavonoid glycoside naringin in human urine. J Agric Food Chem. 2000 Jan;48(1):56-9. [PubMed:10637051 ]
Kanaze FI, Kokkalou E, Georgarakis M, Niopas I: A validated solid-phase extraction HPLC method for the simultaneous determination of the citrus flavanone aglycones hesperetin and naringenin in urine. J Pharm Biomed Anal. 2004 Sep 21;36(1):175-81. [PubMed:15351063 ]

Showing metabocard for Naringin (HMDB0002927)

MOL for HMDB0002927 (Naringin)

3D MOL for HMDB0002927 (Naringin)

3D SDF for HMDB0002927 (Naringin)

3D-SDF for HMDB0002927 (Naringin)

PDB for HMDB0002927 (Naringin)

3D PDB for HMDB0002927 (Naringin)

SMILES for HMDB0002927 (Naringin)

INCHI for HMDB0002927 (Naringin)

Structure for HMDB0002927 (Naringin)

3D Structure for HMDB0002927 (Naringin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra