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Showing metabocard for Naringin (HMDB0002927)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:20 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0002927
Secondary Accession Numbers
  • HMDB02927
Metabolite Identification
Common NameNaringin
DescriptionNaringin, 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002927 (Naringin)


  Mrv1652305271900232D          

 41 45  0  0  1  0            999 V2000
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M  END
Download

3D MOL for HMDB0002927 (Naringin)

HMDB0002927
     RDKit          3D
Naringin
 73 77  0  0  0  0  0  0  0  0999 V2000
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M  END
Download

3D SDF for HMDB0002927 (Naringin)


  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
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   21.7614  -11.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   24.6192  -11.4040    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

$$$$
Download

3D-SDF for HMDB0002927 (Naringin)

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
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 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
Download

PDB for HMDB0002927 (Naringin)

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
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3D PDB for HMDB0002927 (Naringin)

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
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SMILES for HMDB0002927 (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
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INCHI for HMDB0002927 (Naringin)

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
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]ChEBI
Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucosideChEBI
Naringenin 7-O-neohesperidosideChEBI
NaringosideChEBI
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-glucosideGenerator
Naringenin 7-O-α-L-rhamnosyl-(1->2)-β-D-glucosideGenerator
4',5,7-Trihydroxyflavanone 7-rhamnoglucosideMeSH
CyclorelMeSH
AurantiinMeSH
Naringenin-7-hesperidosideMeSH
Naringin dihydrochalconeMeSH
Naringin sodiumMeSH
4'5-DiOH-flavone-7-rhglucHMDB
Naringin hydrateHMDB
NobiletinHMDB
Chemical FormulaC27H32O14
Average Molecular Weight580.5346
Monoisotopic Molecular Weight580.179205732
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 Namenaringin
CAS Registry Number10236-47-2
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 KeyDFPMSGMNTNDNHN-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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point83 °CNot Available
Boiling Point922.00 to 926.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1 mg/mL at 40 °CNot Available
LogP-0.44PERRISSOUD,D & TESTA,B (1986)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker217.32930932474
[M+H]+Baker240.6230932474
[M+H]+MetCCS_train_pos237.45330932474
[M-H]-Not Available217.329http://allccs.zhulab.cn/database/detail?ID=AllCCS00000543
[M+H]+Not Available239.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000543
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.06 g/LALOGPS
logP-0.24ALOGPS
logP-0.16ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)8.58ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area225.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity134.3 m³·mol⁻¹ChemAxon
Polarizability56.19 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+227.15430932474
DeepCCS[M-H]-225.22530932474
DeepCCS[M-2H]-259.03930932474
DeepCCS[M+Na]+233.22530932474
AllCCS[M+H]+228.532859911
AllCCS[M+H-H2O]+227.332859911
AllCCS[M+NH4]+229.632859911
AllCCS[M+Na]+229.932859911
AllCCS[M-H]-222.332859911
AllCCS[M+Na-2H]-224.332859911
AllCCS[M+HCOO]-226.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NaringinC[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]1O5296.7Standard polar33892256
NaringinC[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]1O4704.0Standard non polar33892256
NaringinC[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]1O5202.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Naringin,1TMS,isomer #1C[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]1O4747.1Semi standard non polar33892256
Naringin,1TMS,isomer #2C[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]1O4757.2Semi standard non polar33892256
Naringin,1TMS,isomer #3C[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]1O4766.9Semi standard non polar33892256
Naringin,1TMS,isomer #4C[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]1O4762.6Semi standard non polar33892256
Naringin,1TMS,isomer #5C[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]1O4821.9Semi standard non polar33892256
Naringin,1TMS,isomer #6C[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]1O4754.3Semi standard non polar33892256
Naringin,1TMS,isomer #7C[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]1O4748.7Semi standard non polar33892256
Naringin,1TMS,isomer #8C[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)C4772.6Semi standard non polar33892256
Naringin,2TMS,isomer #1C[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]1O4635.8Semi standard non polar33892256
Naringin,2TMS,isomer #10C[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]1O4667.1Semi standard non polar33892256
Naringin,2TMS,isomer #11C[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]1O4622.2Semi standard non polar33892256
Naringin,2TMS,isomer #12C[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]1O4611.0Semi standard non polar33892256
Naringin,2TMS,isomer #13C[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)C4637.0Semi standard non polar33892256
Naringin,2TMS,isomer #14C[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]1O4665.3Semi standard non polar33892256
Naringin,2TMS,isomer #15C[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]1O4727.0Semi standard non polar33892256
Naringin,2TMS,isomer #16C[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]1O4644.9Semi standard non polar33892256
Naringin,2TMS,isomer #17C[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]1O4634.5Semi standard non polar33892256
Naringin,2TMS,isomer #18C[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)C4662.4Semi standard non polar33892256
Naringin,2TMS,isomer #19C[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]1O4731.5Semi standard non polar33892256
Naringin,2TMS,isomer #2C[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]1O4699.8Semi standard non polar33892256
Naringin,2TMS,isomer #20C[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]1O4636.6Semi standard non polar33892256
Naringin,2TMS,isomer #21C[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]1O4627.9Semi standard non polar33892256
Naringin,2TMS,isomer #22C[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)C4661.4Semi standard non polar33892256
Naringin,2TMS,isomer #23C[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]1O4709.2Semi standard non polar33892256
Naringin,2TMS,isomer #24C[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]1O4698.9Semi standard non polar33892256
Naringin,2TMS,isomer #25C[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)C4726.8Semi standard non polar33892256
Naringin,2TMS,isomer #26C[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]1O4639.7Semi standard non polar33892256
Naringin,2TMS,isomer #27C[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)C4638.0Semi standard non polar33892256
Naringin,2TMS,isomer #28C[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)C4649.1Semi standard non polar33892256
Naringin,2TMS,isomer #3C[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]1O4635.7Semi standard non polar33892256
Naringin,2TMS,isomer #4C[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]1O4646.3Semi standard non polar33892256
Naringin,2TMS,isomer #5C[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]1O4620.5Semi standard non polar33892256
Naringin,2TMS,isomer #6C[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]1O4597.5Semi standard non polar33892256
Naringin,2TMS,isomer #7C[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)C4624.5Semi standard non polar33892256
Naringin,2TMS,isomer #8C[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]1O4645.6Semi standard non polar33892256
Naringin,2TMS,isomer #9C[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]1O4708.4Semi standard non polar33892256
Naringin,3TMS,isomer #1C[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]1O4587.4Semi standard non polar33892256
Naringin,3TMS,isomer #10C[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]1O4556.9Semi standard non polar33892256
Naringin,3TMS,isomer #11C[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)C4581.5Semi standard non polar33892256
Naringin,3TMS,isomer #12C[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]1O4590.8Semi standard non polar33892256
Naringin,3TMS,isomer #13C[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]1O4534.6Semi standard non polar33892256
Naringin,3TMS,isomer #14C[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]1O4510.4Semi standard non polar33892256
Naringin,3TMS,isomer #15C[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)C4546.6Semi standard non polar33892256
Naringin,3TMS,isomer #16C[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]1O4537.5Semi standard non polar33892256
Naringin,3TMS,isomer #17C[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]1O4510.7Semi standard non polar33892256
Naringin,3TMS,isomer #18C[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)C4546.1Semi standard non polar33892256
Naringin,3TMS,isomer #19C[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]1O4525.2Semi standard non polar33892256
Naringin,3TMS,isomer #2C[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]1O4545.1Semi standard non polar33892256
Naringin,3TMS,isomer #20C[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)C4520.6Semi standard non polar33892256
Naringin,3TMS,isomer #21C[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)C4522.7Semi standard non polar33892256
Naringin,3TMS,isomer #22C[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]1O4590.8Semi standard non polar33892256
Naringin,3TMS,isomer #23C[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]1O4567.9Semi standard non polar33892256
Naringin,3TMS,isomer #24C[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]1O4526.7Semi standard non polar33892256
Naringin,3TMS,isomer #25C[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]1O4511.9Semi standard non polar33892256
Naringin,3TMS,isomer #26C[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)C4545.7Semi standard non polar33892256
Naringin,3TMS,isomer #27C[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]1O4620.3Semi standard non polar33892256
Naringin,3TMS,isomer #28C[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]1O4573.9Semi standard non polar33892256
Naringin,3TMS,isomer #29C[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]1O4564.8Semi standard non polar33892256
Naringin,3TMS,isomer #3C[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]1O4551.2Semi standard non polar33892256
Naringin,3TMS,isomer #30C[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)C4589.2Semi standard non polar33892256
Naringin,3TMS,isomer #31C[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]1O4563.1Semi standard non polar33892256
Naringin,3TMS,isomer #32C[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]1O4544.9Semi standard non polar33892256
Naringin,3TMS,isomer #33C[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)C4574.5Semi standard non polar33892256
Naringin,3TMS,isomer #34C[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]1O4527.1Semi standard non polar33892256
Naringin,3TMS,isomer #35C[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)C4523.8Semi standard non polar33892256
Naringin,3TMS,isomer #36C[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)C4527.3Semi standard non polar33892256
Naringin,3TMS,isomer #37C[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]1O4608.1Semi standard non polar33892256
Naringin,3TMS,isomer #38C[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]1O4552.3Semi standard non polar33892256
Naringin,3TMS,isomer #39C[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]1O4539.6Semi standard non polar33892256
Naringin,3TMS,isomer #4C[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]1O4527.8Semi standard non polar33892256
Naringin,3TMS,isomer #40C[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)C4571.5Semi standard non polar33892256
Naringin,3TMS,isomer #41C[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]1O4591.0Semi standard non polar33892256
Naringin,3TMS,isomer #42C[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]1O4582.4Semi standard non polar33892256
Naringin,3TMS,isomer #43C[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)C4608.4Semi standard non polar33892256
Naringin,3TMS,isomer #44C[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]1O4561.4Semi standard non polar33892256
Naringin,3TMS,isomer #45C[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)C4558.0Semi standard non polar33892256
Naringin,3TMS,isomer #46C[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)C4563.5Semi standard non polar33892256
Naringin,3TMS,isomer #47C[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]1O4596.1Semi standard non polar33892256
Naringin,3TMS,isomer #48C[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]1O4584.5Semi standard non polar33892256
Naringin,3TMS,isomer #49C[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)C4610.0Semi standard non polar33892256
Naringin,3TMS,isomer #5C[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]1O4505.5Semi standard non polar33892256
Naringin,3TMS,isomer #50C[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]1O4548.5Semi standard non polar33892256
Naringin,3TMS,isomer #51C[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)C4543.0Semi standard non polar33892256
Naringin,3TMS,isomer #52C[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)C4550.1Semi standard non polar33892256
Naringin,3TMS,isomer #53C[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]1O4593.3Semi standard non polar33892256
Naringin,3TMS,isomer #54C[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)C4586.3Semi standard non polar33892256
Naringin,3TMS,isomer #55C[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)C4590.6Semi standard non polar33892256
Naringin,3TMS,isomer #56C[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)C4561.2Semi standard non polar33892256
Naringin,3TMS,isomer #6C[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)C4538.2Semi standard non polar33892256
Naringin,3TMS,isomer #7C[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]1O4584.8Semi standard non polar33892256
Naringin,3TMS,isomer #8C[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]1O4589.6Semi standard non polar33892256
Naringin,3TMS,isomer #9C[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]1O4570.3Semi standard non polar33892256
Naringin,4TMS,isomer #1C[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]1O4507.5Semi standard non polar33892256
Naringin,4TMS,isomer #10C[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]1O4442.5Semi standard non polar33892256
Naringin,4TMS,isomer #11C[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]1O4422.1Semi standard non polar33892256
Naringin,4TMS,isomer #12C[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)C4449.8Semi standard non polar33892256
Naringin,4TMS,isomer #13C[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]1O4430.5Semi standard non polar33892256
Naringin,4TMS,isomer #14C[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)C4411.7Semi standard non polar33892256
Naringin,4TMS,isomer #15C[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)C4427.7Semi standard non polar33892256
Naringin,4TMS,isomer #16C[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]1O4546.5Semi standard non polar33892256
Naringin,4TMS,isomer #17C[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]1O4499.6Semi standard non polar33892256
Naringin,4TMS,isomer #18C[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]1O4492.7Semi standard non polar33892256
Naringin,4TMS,isomer #19C[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)C4515.1Semi standard non polar33892256
Naringin,4TMS,isomer #2C[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]1O4507.5Semi standard non polar33892256
Naringin,4TMS,isomer #20C[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]1O4495.3Semi standard non polar33892256
Naringin,4TMS,isomer #21C[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]1O4486.4Semi standard non polar33892256
Naringin,4TMS,isomer #22C[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)C4505.3Semi standard non polar33892256
Naringin,4TMS,isomer #23C[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]1O4496.2Semi standard non polar33892256
Naringin,4TMS,isomer #24C[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)C4483.1Semi standard non polar33892256
Naringin,4TMS,isomer #25C[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)C4498.0Semi standard non polar33892256
Naringin,4TMS,isomer #26C[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]1O4490.7Semi standard non polar33892256
Naringin,4TMS,isomer #27C[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]1O4469.6Semi standard non polar33892256
Naringin,4TMS,isomer #28C[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)C4503.1Semi standard non polar33892256
Naringin,4TMS,isomer #29C[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]1O4449.0Semi standard non polar33892256
Naringin,4TMS,isomer #3C[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]1O4495.2Semi standard non polar33892256
Naringin,4TMS,isomer #30C[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)C4433.3Semi standard non polar33892256
Naringin,4TMS,isomer #31C[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)C4453.0Semi standard non polar33892256
Naringin,4TMS,isomer #32C[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]1O4442.8Semi standard non polar33892256
Naringin,4TMS,isomer #33C[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)C4427.7Semi standard non polar33892256
Naringin,4TMS,isomer #34C[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)C4446.1Semi standard non polar33892256
Naringin,4TMS,isomer #35C[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)C4436.0Semi standard non polar33892256
Naringin,4TMS,isomer #36C[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]1O4526.2Semi standard non polar33892256
Naringin,4TMS,isomer #37C[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]1O4499.9Semi standard non polar33892256
Naringin,4TMS,isomer #38C[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]1O4500.1Semi standard non polar33892256
Naringin,4TMS,isomer #39C[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)C4516.8Semi standard non polar33892256
Naringin,4TMS,isomer #4C[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]1O4495.4Semi standard non polar33892256
Naringin,4TMS,isomer #40C[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]1O4468.3Semi standard non polar33892256
Naringin,4TMS,isomer #41C[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]1O4448.7Semi standard non polar33892256
Naringin,4TMS,isomer #42C[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)C4480.7Semi standard non polar33892256
Naringin,4TMS,isomer #43C[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]1O4432.8Semi standard non polar33892256
Naringin,4TMS,isomer #44C[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)C4419.8Semi standard non polar33892256
Naringin,4TMS,isomer #45C[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)C4434.5Semi standard non polar33892256
Naringin,4TMS,isomer #46C[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]1O4526.6Semi standard non polar33892256
Naringin,4TMS,isomer #47C[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]1O4517.3Semi standard non polar33892256
Naringin,4TMS,isomer #48C[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)C4541.2Semi standard non polar33892256
Naringin,4TMS,isomer #49C[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]1O4498.1Semi standard non polar33892256
Naringin,4TMS,isomer #5C[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)C4512.4Semi standard non polar33892256
Naringin,4TMS,isomer #50C[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)C4493.6Semi standard non polar33892256
Naringin,4TMS,isomer #51C[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)C4499.6Semi standard non polar33892256
Naringin,4TMS,isomer #52C[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]1O4473.3Semi standard non polar33892256
Naringin,4TMS,isomer #53C[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)C4461.8Semi standard non polar33892256
Naringin,4TMS,isomer #54C[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)C4477.0Semi standard non polar33892256
Naringin,4TMS,isomer #55C[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)C4447.0Semi standard non polar33892256
Naringin,4TMS,isomer #56C[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]1O4510.9Semi standard non polar33892256
Naringin,4TMS,isomer #57C[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]1O4504.8Semi standard non polar33892256
Naringin,4TMS,isomer #58C[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)C4525.3Semi standard non polar33892256
Naringin,4TMS,isomer #59C[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]1O4477.0Semi standard non polar33892256
Naringin,4TMS,isomer #6C[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]1O4500.3Semi standard non polar33892256
Naringin,4TMS,isomer #60C[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)C4458.3Semi standard non polar33892256
Naringin,4TMS,isomer #61C[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)C4475.8Semi standard non polar33892256
Naringin,4TMS,isomer #62C[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]1O4517.8Semi standard non polar33892256
Naringin,4TMS,isomer #63C[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)C4509.9Semi standard non polar33892256
Naringin,4TMS,isomer #64C[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)C4520.5Semi standard non polar33892256
Naringin,4TMS,isomer #65C[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)C4491.7Semi standard non polar33892256
Naringin,4TMS,isomer #66C[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]1O4514.5Semi standard non polar33892256
Naringin,4TMS,isomer #67C[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)C4506.9Semi standard non polar33892256
Naringin,4TMS,isomer #68C[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)C4515.7Semi standard non polar33892256
Naringin,4TMS,isomer #69C[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)C4464.7Semi standard non polar33892256
Naringin,4TMS,isomer #7C[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]1O4451.6Semi standard non polar33892256
Naringin,4TMS,isomer #70C[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)C4509.4Semi standard non polar33892256
Naringin,4TMS,isomer #8C[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]1O4431.7Semi standard non polar33892256
Naringin,4TMS,isomer #9C[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)C4460.9Semi standard non polar33892256
Naringin,1TBDMS,isomer #1C[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]1O4976.5Semi standard non polar33892256
Naringin,1TBDMS,isomer #2C[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]1O4985.1Semi standard non polar33892256
Naringin,1TBDMS,isomer #3C[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]1O5007.7Semi standard non polar33892256
Naringin,1TBDMS,isomer #4C[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]1O5008.0Semi standard non polar33892256
Naringin,1TBDMS,isomer #5C[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]1O5069.1Semi standard non polar33892256
Naringin,1TBDMS,isomer #6C[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]1O4988.3Semi standard non polar33892256
Naringin,1TBDMS,isomer #7C[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]1O4991.2Semi standard non polar33892256
Naringin,1TBDMS,isomer #8C[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)C5009.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #1C[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]1O5072.3Semi standard non polar33892256
Naringin,2TBDMS,isomer #10C[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]1O5088.2Semi standard non polar33892256
Naringin,2TBDMS,isomer #11C[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]1O5062.3Semi standard non polar33892256
Naringin,2TBDMS,isomer #12C[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]1O5056.9Semi standard non polar33892256
Naringin,2TBDMS,isomer #13C[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)C5077.5Semi standard non polar33892256
Naringin,2TBDMS,isomer #14C[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]1O5092.9Semi standard non polar33892256
Naringin,2TBDMS,isomer #15C[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]1O5149.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #16C[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]1O5084.0Semi standard non polar33892256
Naringin,2TBDMS,isomer #17C[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]1O5081.2Semi standard non polar33892256
Naringin,2TBDMS,isomer #18C[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)C5103.3Semi standard non polar33892256
Naringin,2TBDMS,isomer #19C[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]1O5159.1Semi standard non polar33892256
Naringin,2TBDMS,isomer #2C[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]1O5131.4Semi standard non polar33892256
Naringin,2TBDMS,isomer #20C[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]1O5083.9Semi standard non polar33892256
Naringin,2TBDMS,isomer #21C[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]1O5087.1Semi standard non polar33892256
Naringin,2TBDMS,isomer #22C[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)C5107.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #23C[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]1O5149.0Semi standard non polar33892256
Naringin,2TBDMS,isomer #24C[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]1O5148.8Semi standard non polar33892256
Naringin,2TBDMS,isomer #25C[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)C5168.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #26C[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]1O5076.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #27C[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)C5084.4Semi standard non polar33892256
Naringin,2TBDMS,isomer #28C[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)C5088.9Semi standard non polar33892256
Naringin,2TBDMS,isomer #3C[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]1O5074.3Semi standard non polar33892256
Naringin,2TBDMS,isomer #4C[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]1O5061.0Semi standard non polar33892256
Naringin,2TBDMS,isomer #5C[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]1O5067.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #6C[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]1O5053.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #7C[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)C5073.2Semi standard non polar33892256
Naringin,2TBDMS,isomer #8C[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]1O5071.2Semi standard non polar33892256
Naringin,2TBDMS,isomer #9C[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]1O5137.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Naringin GC-EI-TOF (Non-derivatized)splash10-014j-0920000000-350bda4f263e4440e76a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naringin GC-EI-TOF (Non-derivatized)splash10-014j-0920000000-350bda4f263e4440e76a2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (Non-derivatized) - 70eV, Positivesplash10-044j-9521280000-3e3e40b7d28b4e9032162017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (1 TMS) - 70eV, Positivesplash10-00ei-9302015000-e97b650a0d6a1b78ddc32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS ("Naringin,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0000090000-62ab85e8b85e9515ddc12012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin LC-ESI-ITTOF (Shimadzu LC20A-IT-TOFMS) , Negative-QTOFsplash10-004i-0000091000-2671e4ecb91933035e782012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 10V, Negative-QTOFsplash10-004i-0100090000-0c16a31fd116a04809ff2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 40V, Negative-QTOFsplash10-00di-0290110000-a72cef11c1816469a2692017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 10V, Negative-QTOFsplash10-00di-0290110000-a72cef11c1816469a2692017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 20V, Negative-QTOFsplash10-004i-0000090000-d6285c4e4374990ed1612017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 30V, Negative-QTOFsplash10-004i-0030290000-06238e4a98a4daad32652017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 50V, Negative-QTOFsplash10-004i-0030290000-06238e4a98a4daad32652017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 10V, Negative-QTOFsplash10-004i-0100090000-0c16a31fd116a04809ff2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 40V, Negative-QTOFsplash10-00di-0290110000-a72cef11c1816469a2692017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 10V, Negative-QTOFsplash10-004i-0000090000-4498c4e102c3c7d3d5142017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 20V, Negative-QTOFsplash10-004i-0000090000-d6285c4e4374990ed1612017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 30V, Negative-QTOFsplash10-004i-0030290000-06238e4a98a4daad32652017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 50V, Negative-QTOFsplash10-0fk9-0690000000-3d8f024f57318d3dbca82017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin LC-ESI-qTof , Positive-QTOFsplash10-0fk9-2981000000-e103705338e8e88553072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin LC-ESI-TOF , negative-QTOFsplash10-00di-0290110000-a72cef11c1816469a2692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin LC-ESI-TOF , negative-QTOFsplash10-004i-0000090000-4498c4e102c3c7d3d5142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin LC-ESI-TOF , negative-QTOFsplash10-004i-0000090000-d6285c4e4374990ed1612017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin LC-ESI-TOF , negative-QTOFsplash10-004i-0030290000-06238e4a98a4daad32652017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringin 10V, Positive-QTOFsplash10-00xr-0390740000-ed6375341eb1bebac3192017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringin 20V, Positive-QTOFsplash10-05fr-0490200000-bbf5e62f8ba5ef5c55c62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringin 40V, Positive-QTOFsplash10-01b9-0940000000-043fddfc9269db83e1f12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringin 10V, Negative-QTOFsplash10-02or-3592880000-a3ec8e8504154578e09f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringin 20V, Negative-QTOFsplash10-0229-2691310000-865585e62bd05144335b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringin 40V, Negative-QTOFsplash10-00di-7590000000-82ba5c0120e07b81e87b2017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Urine
Tissue Locations
  • Epidermis
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 208 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID208
FooDB IDFDB011866
KNApSAcK IDC00000983
Chemspider ID390868
KEGG Compound IDC09789
BioCyc IDNARINGIN
BiGG IDNot Available
Wikipedia LinkNaringin
METLIN ID3604
PubChem Compound442428
PDB IDNot Available
ChEBI ID28819
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1400021
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]