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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:18:58 UTC

Update Date

2022-03-07 02:56:20 UTC

HMDB ID

HMDB0039776

Secondary Accession Numbers

HMDB39776

Metabolite Identification

Common Name

6''-O-Malonylnaringin

Description

6''-O-Malonylnaringin 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. 6''-O-Malonylnaringin is found, on average, in the highest concentration within grapefruit/pummelo hybrids (Citrus paradisi X Citrus maxima). 6''-O-Malonylnaringin has also been detected, but not quantified in, citrus. This could make 6''-O-malonylnaringin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6''-O-Malonylnaringin.

Structure

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

Naringin 6&apos;-malonate
  Mrv1572001071617302D          

 47 51  0  0  0  0            999 V2000
    0.0000    0.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.4037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.0537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -5.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.7662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.7662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.8787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.0713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.8963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.0713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
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 11 20  1  0  0  0  0
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  6 21  1  0  0  0  0
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 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 32 38  1  0  0  0  0
 26 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 23 41  1  0  0  0  0
  4 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
  2 46  1  0  0  0  0
 46 47  1  0  0  0  0
M  END

HMDB0039776
     RDKit          3D
6''-O-Malonylnaringin
 81 85  0  0  0  0  0  0  0  0999 V2000
   -2.4040   -4.9613    2.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850   -3.6174    1.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958   -3.6016    0.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -2.5936   -0.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818   -1.4607    0.2933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3477   -0.3593   -0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1775    0.0679    0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0289    0.3236   -0.1504 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1720   -0.3471   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4653   -1.4186    0.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7183   -2.0412    0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9945   -3.1239    1.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7225   -1.6001   -0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4434   -0.5318   -0.9422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2061    0.0892   -0.9372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4501   -0.0667   -1.7971 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7933   -0.5065   -1.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6325    0.3654   -0.9047 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667    1.7439   -1.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3375    2.5931   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1956    2.1106    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9852    2.9688    1.4464 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2664    0.7453    0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4852   -0.1145    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8785   -1.9681   -1.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0357   -2.2164   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4182   -2.9244    0.7884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4284    1.0868    1.4252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0395    2.2349    0.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517    3.0582    0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6052    4.2379   -0.3528 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2487    4.0797   -1.8430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    6.2774   -1.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6904    6.6226   -2.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9762    7.9483   -2.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3436    0.7068   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641    1.0988   -1.8732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3016   -3.1145   -0.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2175   -2.8680    0.5006 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7836   -4.3646    2.5677 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3243   -2.5038   -2.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1006   -4.0259   -1.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5084   -2.0040   -2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7326   -2.9137   -0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5282   -2.4239    2.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7620   -5.2393    2.0936 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
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 44 78  1  0
 45 79  1  0
 46 80  1  0
 47 81  1  0
M  END

Naringin 6&apos;-malonate
  Mrv1572001071617302D          

 47 51  0  0  0  0            999 V2000
    0.0000    0.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.4037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.0537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -2.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289    2.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.8963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.0713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
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  4 42  1  0  0  0  0
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 44 46  1  0  0  0  0
  2 46  1  0  0  0  0
 46 47  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039776

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC(OC2C(O)C(O)C(COC(=O)CC(O)=O)OC2OC2=CC3=C(C(=O)CC(O3)C3=CC=C(O)C=C3)C(O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H34O17/c1-11-23(37)25(39)27(41)29(43-11)47-28-26(40)24(38)19(10-42-21(36)9-20(34)35)46-30(28)44-14-6-15(32)22-16(33)8-17(45-18(22)7-14)12-2-4-13(31)5-3-12/h2-7,11,17,19,23-32,37-41H,8-10H2,1H3,(H,34,35)

> <INCHI_KEY>
YCOQCRMFNLZUCL-UHFFFAOYSA-N

> <FORMULA>
C30H34O17

> <MOLECULAR_WEIGHT>
666.585

> <EXACT_MASS>
666.179599635

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
64.10603672096664

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methoxy]-3-oxopropanoic acid

> <ALOGPS_LOGP>
0.39

> <JCHEM_LOGP>
0.17646813433333486

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.579346622872155

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3730318103290737

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121826294490695

> <JCHEM_POLAR_SURFACE_AREA>
268.42999999999995

> <JCHEM_REFRACTIVITY>
149.7994

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methoxy]-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039776
     RDKit          3D
6''-O-Malonylnaringin
 81 85  0  0  0  0  0  0  0  0999 V2000
   -2.4040   -4.9613    2.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5942    2.5859    2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
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 47 81  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Naringin 6&apos;-malonate                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       0.000   0.786   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   1.556   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667   0.786   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.001   1.556   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.335   0.786   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.335  -0.754   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668  -1.524   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -8.002  -0.754   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.668  -3.064   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -8.002  -3.834   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.335  -3.834   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  -5.374   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.668  -6.144   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.668  -7.684   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.335  -8.454   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -8.002  -8.454   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002  -9.994   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.336 -10.764   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.668 -10.764   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.001  -3.064   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.001  -1.524   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.667  -0.754   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334  -1.524   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -0.754   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -1.524   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -3.064   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -3.834   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667  -5.374   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -3.064   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -1.524   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667  -0.754   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.335  -0.754   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668  -1.524   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002  -0.754   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002   0.786   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336   1.556   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.668   1.556   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.335   0.786   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.000  -3.834   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.000  -5.374   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -1.334  -3.064   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -4.001   3.096   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -5.335   3.866   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -2.667   3.866   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -2.667   5.406   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -1.334   3.096   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       0.000   3.866   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   46                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   42                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   11   21                                                       
CONECT   21   20    6   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   41                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27   39                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30   25                                                       
CONECT   32   30   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   32                                                       
CONECT   39   26   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   23                                                       
CONECT   42    4   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44    2   47                                                  
CONECT   47   46                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  102    0
END

COMPND    HMDB0039776
HETATM    1  C1  UNL     1      -2.404  -4.961   2.168  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.785  -3.617   1.533  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.296  -3.602   0.243  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.922  -2.594  -0.484  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.982  -1.461   0.293  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.348  -0.359  -0.274  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.177   0.068   0.572  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.029   0.324  -0.150  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.172  -0.347  -0.096  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.465  -1.419   0.713  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.718  -2.041   0.703  1.00  0.00           C  
HETATM   12  O4  UNL     1       2.995  -3.124   1.529  1.00  0.00           O  
HETATM   13  C9  UNL     1       3.722  -1.600  -0.130  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.443  -0.532  -0.942  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.206   0.089  -0.937  1.00  0.00           C  
HETATM   16  O5  UNL     1       4.450  -0.067  -1.797  1.00  0.00           O  
HETATM   17  C12 UNL     1       5.793  -0.507  -1.742  1.00  0.00           C  
HETATM   18  C13 UNL     1       6.633   0.365  -0.905  1.00  0.00           C  
HETATM   19  C14 UNL     1       6.567   1.744  -1.073  1.00  0.00           C  
HETATM   20  C15 UNL     1       7.337   2.593  -0.302  1.00  0.00           C  
HETATM   21  C16 UNL     1       8.196   2.111   0.657  1.00  0.00           C  
HETATM   22  O6  UNL     1       8.985   2.969   1.446  1.00  0.00           O  
HETATM   23  C17 UNL     1       8.266   0.745   0.830  1.00  0.00           C  
HETATM   24  C18 UNL     1       7.485  -0.114   0.049  1.00  0.00           C  
HETATM   25  C19 UNL     1       5.879  -1.968  -1.386  1.00  0.00           C  
HETATM   26  C20 UNL     1       5.036  -2.216  -0.172  1.00  0.00           C  
HETATM   27  O7  UNL     1       5.418  -2.924   0.788  1.00  0.00           O  
HETATM   28  O8  UNL     1      -1.428   1.087   1.425  1.00  0.00           O  
HETATM   29  C21 UNL     1      -2.040   2.235   0.914  1.00  0.00           C  
HETATM   30  C22 UNL     1      -1.152   3.058   0.084  1.00  0.00           C  
HETATM   31  O9  UNL     1      -1.605   4.238  -0.353  1.00  0.00           O  
HETATM   32  C23 UNL     1      -2.492   4.790  -1.162  1.00  0.00           C  
HETATM   33  O10 UNL     1      -3.249   4.080  -1.843  1.00  0.00           O  
HETATM   34  C24 UNL     1      -2.626   6.277  -1.296  1.00  0.00           C  
HETATM   35  C25 UNL     1      -3.690   6.623  -2.269  1.00  0.00           C  
HETATM   36  O11 UNL     1      -4.356   5.739  -2.864  1.00  0.00           O  
HETATM   37  O12 UNL     1      -3.976   7.948  -2.546  1.00  0.00           O  
HETATM   38  C26 UNL     1      -3.379   1.831   0.447  1.00  0.00           C  
HETATM   39  O13 UNL     1      -3.989   1.233   1.624  1.00  0.00           O  
HETATM   40  C27 UNL     1      -3.344   0.707  -0.540  1.00  0.00           C  
HETATM   41  O14 UNL     1      -3.264   1.099  -1.873  1.00  0.00           O  
HETATM   42  C28 UNL     1      -4.302  -3.114  -0.843  1.00  0.00           C  
HETATM   43  O15 UNL     1      -5.005  -2.189  -1.588  1.00  0.00           O  
HETATM   44  C29 UNL     1      -5.023  -3.596   0.372  1.00  0.00           C  
HETATM   45  O16 UNL     1      -6.218  -2.868   0.501  1.00  0.00           O  
HETATM   46  C30 UNL     1      -4.262  -3.425   1.647  1.00  0.00           C  
HETATM   47  O17 UNL     1      -4.784  -4.365   2.568  1.00  0.00           O  
HETATM   48  H1  UNL     1      -2.993  -5.019   3.115  1.00  0.00           H  
HETATM   49  H2  UNL     1      -1.310  -4.931   2.361  1.00  0.00           H  
HETATM   50  H3  UNL     1      -2.689  -5.757   1.454  1.00  0.00           H  
HETATM   51  H4  UNL     1      -2.283  -2.774   2.072  1.00  0.00           H  
HETATM   52  H5  UNL     1      -2.356  -2.346  -1.409  1.00  0.00           H  
HETATM   53  H6  UNL     1      -1.950  -0.728  -1.265  1.00  0.00           H  
HETATM   54  H7  UNL     1      -0.966  -0.835   1.229  1.00  0.00           H  
HETATM   55  H8  UNL     1       0.710  -1.795   1.379  1.00  0.00           H  
HETATM   56  H9  UNL     1       2.249  -3.439   2.136  1.00  0.00           H  
HETATM   57  H10 UNL     1       2.016   0.922  -1.584  1.00  0.00           H  
HETATM   58  H11 UNL     1       6.160  -0.425  -2.811  1.00  0.00           H  
HETATM   59  H12 UNL     1       5.887   2.132  -1.834  1.00  0.00           H  
HETATM   60  H13 UNL     1       7.278   3.679  -0.443  1.00  0.00           H  
HETATM   61  H14 UNL     1       9.594   2.586   2.128  1.00  0.00           H  
HETATM   62  H15 UNL     1       8.930   0.314   1.576  1.00  0.00           H  
HETATM   63  H16 UNL     1       7.556  -1.176   0.205  1.00  0.00           H  
HETATM   64  H17 UNL     1       6.905  -2.301  -1.299  1.00  0.00           H  
HETATM   65  H18 UNL     1       5.324  -2.504  -2.213  1.00  0.00           H  
HETATM   66  H19 UNL     1      -2.229   2.854   1.865  1.00  0.00           H  
HETATM   67  H20 UNL     1      -0.639   2.441  -0.733  1.00  0.00           H  
HETATM   68  H21 UNL     1      -0.242   3.281   0.750  1.00  0.00           H  
HETATM   69  H22 UNL     1      -2.852   6.749  -0.315  1.00  0.00           H  
HETATM   70  H23 UNL     1      -1.658   6.690  -1.635  1.00  0.00           H  
HETATM   71  H24 UNL     1      -4.692   8.456  -2.053  1.00  0.00           H  
HETATM   72  H25 UNL     1      -4.047   2.621   0.113  1.00  0.00           H  
HETATM   73  H26 UNL     1      -3.860   1.907   2.364  1.00  0.00           H  
HETATM   74  H27 UNL     1      -4.383   0.238  -0.471  1.00  0.00           H  
HETATM   75  H28 UNL     1      -4.130   1.491  -2.130  1.00  0.00           H  
HETATM   76  H29 UNL     1      -4.101  -4.026  -1.483  1.00  0.00           H  
HETATM   77  H30 UNL     1      -4.508  -2.004  -2.411  1.00  0.00           H  
HETATM   78  H31 UNL     1      -5.342  -4.667   0.294  1.00  0.00           H  
HETATM   79  H32 UNL     1      -6.733  -2.914  -0.355  1.00  0.00           H  
HETATM   80  H33 UNL     1      -4.528  -2.424   2.093  1.00  0.00           H  
HETATM   81  H34 UNL     1      -4.762  -5.239   2.094  1.00  0.00           H  
CONECT    1    2   48   49   50
CONECT    2    3   46   51
CONECT    3    4
CONECT    4    5   42   52
CONECT    5    6
CONECT    6    7   40   53
CONECT    7    8   28   54
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   55
CONECT   11   12   13   13
CONECT   12   56
CONECT   13   14   26
CONECT   14   15   15   16
CONECT   15   57
CONECT   16   17
CONECT   17   18   25   58
CONECT   18   19   19   24
CONECT   19   20   59
CONECT   20   21   21   60
CONECT   21   22   23
CONECT   22   61
CONECT   23   24   24   62
CONECT   24   63
CONECT   25   26   64   65
CONECT   26   27   27
CONECT   28   29
CONECT   29   30   38   66
CONECT   30   31   67   68
CONECT   31   32
CONECT   32   33   33   34
CONECT   34   35   69   70
CONECT   35   36   36   37
CONECT   37   71
CONECT   38   39   40   72
CONECT   39   73
CONECT   40   41   74
CONECT   41   75
CONECT   42   43   44   76
CONECT   43   77
CONECT   44   45   46   78
CONECT   45   79
CONECT   46   47   80
CONECT   47   81
END

HMDB0039776
     RDKit          3D
6''-O-Malonylnaringin
 81 85  0  0  0  0  0  0  0  0999 V2000
   -2.4040   -4.9613    2.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850   -3.6174    1.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958   -3.6016    0.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -2.5936   -0.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818   -1.4607    0.2933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3477   -0.3593   -0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1775    0.0679    0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0289    0.3236   -0.1504 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1720   -0.3471   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4653   -1.4186    0.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7183   -2.0412    0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9945   -3.1239    1.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7225   -1.6001   -0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4434   -0.5318   -0.9422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2061    0.0892   -0.9372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4501   -0.0667   -1.7971 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7933   -0.5065   -1.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6325    0.3654   -0.9047 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667    1.7439   -1.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3375    2.5931   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1956    2.1106    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9852    2.9688    1.4464 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2664    0.7453    0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4852   -0.1145    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8785   -1.9681   -1.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0357   -2.2164   -0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4182   -2.9244    0.7884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4284    1.0868    1.4252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0395    2.2349    0.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517    3.0582    0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6052    4.2379   -0.3528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921    4.7904   -1.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2487    4.0797   -1.8430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    6.2774   -1.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6904    6.6226   -2.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3561    5.7386   -2.8637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9762    7.9483   -2.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3787    1.8306    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9892    1.2328    1.6239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3436    0.7068   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641    1.0988   -1.8732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3016   -3.1145   -0.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0047   -2.1891   -1.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0225   -3.5964    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2175   -2.8680    0.5006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2616   -3.4247    1.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7836   -4.3646    2.5677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9929   -5.0194    3.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3097   -4.9306    2.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6894   -5.7566    1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2830   -2.7739    2.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3556   -2.3462   -1.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9504   -0.7277   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9661   -0.8346    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7098   -1.7954    1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2491   -3.4388    2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0162    0.9221   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1604   -0.4252   -2.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8867    2.1319   -1.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2781    3.6795   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5942    2.5859    2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9298    0.3138    1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5556   -1.1758    0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9052   -2.3006   -1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3243   -2.5038   -2.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2290    2.8540    1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6394    2.4409   -0.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2420    3.2809    0.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8522    6.7491   -0.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6582    6.6902   -1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6920    8.4564   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0467    2.6210    0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8599    1.9068    2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3826    0.2382   -0.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1298    1.4908   -2.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1006   -4.0259   -1.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5084   -2.0040   -2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3421   -4.6671    0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7326   -2.9137   -0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5282   -2.4239    2.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7620   -5.2393    2.0936 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
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 13 14  1  0
 14 15  2  0
 14 16  1  0
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  7 28  1  0
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  4 42  1  0
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 40  6  1  0
 15  9  1  0
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  1 48  1  0
  1 49  1  0
  1 50  1  0
  2 51  1  0
  4 52  1  0
  6 53  1  0
  7 54  1  0
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 37 71  1  0
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 44 78  1  0
 45 79  1  0
 46 80  1  0
 47 81  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Naringin 6''-malonate	HMDB
3-[(3,4-Dihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methoxy]-3-oxopropanoate	Generator
Naringin 6''-malonic acid	Generator

Chemical Formula

C₃₀H₃₄O₁₇

Average Molecular Weight

666.585

Monoisotopic Molecular Weight

666.179599635

IUPAC Name

3-[(3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methoxy]-3-oxopropanoic acid

Traditional Name

3-[(3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methoxy]-3-oxopropanoic acid

CAS Registry Number

139934-59-1

SMILES

CC1OC(OC2C(O)C(O)C(COC(=O)CC(O)=O)OC2OC2=CC3=C(C(=O)CC(O3)C3=CC=C(O)C=C3)C(O)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C30H34O17/c1-11-23(37)25(39)27(41)29(43-11)47-28-26(40)24(38)19(10-42-21(36)9-20(34)35)46-30(28)44-14-6-15(32)22-16(33)8-17(45-18(22)7-14)12-2-4-13(31)5-3-12/h2-7,11,17,19,23-32,37-41H,8-10H2,1H3,(H,34,35)

InChI Key

YCOQCRMFNLZUCL-UHFFFAOYSA-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
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Flavan
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Chromone
Disaccharide
Chromane
1-benzopyran
Benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Oxane
1,3-dicarbonyl compound
Benzenoid
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Ketone
Polyol
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Ether
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039776)
Cytoplasm (HMDB: HMDB0039776)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039776)

Source

Exogenous

Food

Food (HMDB: HMDB0039776)

Fruit

Citrus

Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0039776)

Not Available

Nutrient (HMDB: HMDB0039776)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.93 g/L	ALOGPS
logP	0.39	ALOGPS
logP	0.18	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	268.43 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	149.8 m³·mol⁻¹	ChemAxon
Polarizability	64.11 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
DarkChem	[M+H]+	249.177	31661259
DarkChem	[M-H]-	235.872	31661259
DeepCCS	[M+H]+	240.853	30932474
DeepCCS	[M-H]-	239.001	30932474
DeepCCS	[M-2H]-	272.242	30932474
DeepCCS	[M+Na]+	246.594	30932474
AllCCS	[M+H]+	241.0	32859911
AllCCS	[M+H-H2O]+	240.2	32859911
AllCCS	[M+NH4]+	241.6	32859911
AllCCS	[M+Na]+	241.8	32859911
AllCCS	[M-H]-	236.1	32859911
AllCCS	[M+Na-2H]-	239.0	32859911
AllCCS	[M+HCOO]-	242.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6''-O-Malonylnaringin	CC1OC(OC2C(O)C(O)C(COC(=O)CC(O)=O)OC2OC2=CC3=C(C(=O)CC(O3)C3=CC=C(O)C=C3)C(O)=C2)C(O)C(O)C1O	6093.4	Standard polar	33892256
6''-O-Malonylnaringin	CC1OC(OC2C(O)C(O)C(COC(=O)CC(O)=O)OC2OC2=CC3=C(C(=O)CC(O3)C3=CC=C(O)C=C3)C(O)=C2)C(O)C(O)C1O	4875.7	Standard non polar	33892256
6''-O-Malonylnaringin	CC1OC(OC2C(O)C(O)C(COC(=O)CC(O)=O)OC2OC2=CC3=C(C(=O)CC(O3)C3=CC=C(O)C=C3)C(O)=C2)C(O)C(O)C1O	5809.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9411025000-e61e5aad6ddbbf631a09	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_1_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6''-O-Malonylnaringin GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6''-O-Malonylnaringin 10V, Positive-QTOF	splash10-00di-2290276000-01b959315d520489dcf8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6''-O-Malonylnaringin 20V, Positive-QTOF	splash10-00di-1290220000-7cf77b84e6c232e82501	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6''-O-Malonylnaringin 40V, Positive-QTOF	splash10-00dj-2791100000-a4e4308d4d5d65f069fa	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6''-O-Malonylnaringin 10V, Negative-QTOF	splash10-0v59-9741056000-1d0e8fd01f3b3f4140a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6''-O-Malonylnaringin 20V, Negative-QTOF	splash10-0uk9-7960121000-9fb145aa8aa21671c13f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6''-O-Malonylnaringin 40V, Negative-QTOF	splash10-0fk9-8970000000-f8d522c255d95627dfea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6''-O-Malonylnaringin 10V, Positive-QTOF	splash10-014i-0000009000-bc98793c03f31e725a64	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6''-O-Malonylnaringin 20V, Positive-QTOF	splash10-0002-0400096000-7cc3aaff91be95f19061	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6''-O-Malonylnaringin 40V, Positive-QTOF	splash10-0002-0300090000-1a26f7b589b00f122175	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6''-O-Malonylnaringin 10V, Negative-QTOF	splash10-014i-0000009000-64e48093b0aecd888e4f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6''-O-Malonylnaringin 20V, Negative-QTOF	splash10-014j-0000098000-69e26aefaf55f38ae579	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6''-O-Malonylnaringin 40V, Negative-QTOF	splash10-014i-0900040000-f267913b8a6f1bc610c3	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

217

FooDB ID

FDB019425

KNApSAcK ID

C00008530

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74819370

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 6''-O-Malonylnaringin (HMDB0039776)

MOL for HMDB0039776 (6''-O-Malonylnaringin)

3D MOL for HMDB0039776 (6''-O-Malonylnaringin)

3D SDF for HMDB0039776 (6''-O-Malonylnaringin)

3D-SDF for HMDB0039776 (6''-O-Malonylnaringin)

PDB for HMDB0039776 (6''-O-Malonylnaringin)

3D PDB for HMDB0039776 (6''-O-Malonylnaringin)

SMILES for HMDB0039776 (6''-O-Malonylnaringin)

INCHI for HMDB0039776 (6''-O-Malonylnaringin)

Structure for HMDB0039776 (6''-O-Malonylnaringin)

3D Structure for HMDB0039776 (6''-O-Malonylnaringin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra