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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:09:11 UTC

Update Date

2021-09-23 03:09:11 UTC

HMDB ID

HMDB0301863

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Apigenin 7-(6''-malonylglucoside)

Description

Apigenin 7-(6''-malonylglucoside) is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Apigenin 7-(6''-malonylglucoside) is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Apigenin 7-(6''-malonylglucoside) can be found in german camomile, lupine, and parsley, which makes apigenin 7-(6''-malonylglucoside) a potential biomarker for the consumption of these food products.

Structure

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


  Mrv0541 02241221022D          

 38 41  0  0  0  0            999 V2000
   -0.7145   -2.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.5822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.5822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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 35 38  2  0  0  0  0
M  END

HMDB0301863
     RDKit          3D
Apigenin 7-(6''-malonylglucoside)
 60 63  0  0  0  0  0  0  0  0999 V2000
    9.8912    0.2505   -0.8921 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7782    2.3680    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
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 37  9  1  0
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 29 23  1  0
  3 39  1  0
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M  END


  Mrv0541 02241221022D          

 38 41  0  0  0  0            999 V2000
   -0.7145   -2.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -2.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.5822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 37  2  0  0  0  0
 35 38  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301863

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1[C@H](O)[C@@H](COC(=O)CC(O)=O)O[C@@H](OC2=CC(O)=C3C(OC(=C(O)C3=O)C3=CC=C(O)C=C3)=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O14/c25-10-3-1-9(2-4-10)23-21(33)19(31)17-12(26)5-11(6-13(17)37-23)36-24-22(34)20(32)18(30)14(38-24)8-35-16(29)7-15(27)28/h1-6,14,18,20,22,24-26,30,32-34H,7-8H2,(H,27,28)/t14-,18-,20+,22-,24-/m1/s1

> <INCHI_KEY>
FIVFPODHFQLHTO-ZQIGZIPLSA-N

> <FORMULA>
C24H22O14

> <MOLECULAR_WEIGHT>
534.4231

> <EXACT_MASS>
534.100955412

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
49.880437279109486

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3-oxopropanoic acid

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
0.5251505486666666

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.461231687131363

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.367938132485547

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649103025442529

> <JCHEM_POLAR_SURFACE_AREA>
229.73999999999998

> <JCHEM_REFRACTIVITY>
122.52129999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301863
     RDKit          3D
Apigenin 7-(6''-malonylglucoside)
 60 63  0  0  0  0  0  0  0  0999 V2000
    9.8912    0.2505   -0.8921 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6940   -0.1452   -0.9838 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6505    0.6811   -0.5455 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4609   -1.4825   -1.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0198   -1.8132   -1.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6824   -2.9298   -2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0245   -0.9729   -1.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6455   -1.3171   -1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7996   -0.1667   -0.6501 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5034   -0.5434   -0.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7136   -0.2492    0.3815 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4021   -0.5782    0.1870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6952    0.2313    0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376    1.5822    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782    2.3680    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121    3.7380    0.6723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0220    1.7932    0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1313    2.6029    0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0247    3.8367    0.4412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3735    1.9892   -0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4675    2.8103    0.0106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4205    0.6401   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6751   -0.0694   -0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9173    0.5059   -0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0852   -0.2293   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9533   -1.5730   -0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0965   -2.3274   -1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7109   -2.1951   -0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6134   -1.4417   -0.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2995   -0.0847   -0.2347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1230    0.4386   -0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735   -0.2882   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702   -1.0613    1.5148 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5266   -1.2324    2.5748 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5837   -0.2146    1.8666 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3638   -0.8530    2.8359 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510    0.1918    0.6692 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5299    1.5848    0.7070 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8804    1.3779    0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8507   -1.4531   -2.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0118   -2.2753   -0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208   -2.2105   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662   -1.5453   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9547    0.6709   -1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8478    0.8278    0.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3143    2.0705    0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8273    4.1742    0.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4409    3.7876    0.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0342    1.5510   -0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0211    0.2785   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5929   -2.7383   -0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6885   -3.2608   -1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6532   -1.9415   -0.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0536   -1.3562   -0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7707   -2.0216    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -1.6576    2.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1603    0.6857    2.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9420   -0.1343    3.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3988   -0.2174    0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0889    1.9114   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 22 30  1  0
 30 31  1  0
 31 32  2  0
 11 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37  9  1  0
 32 13  1  0
 31 17  1  0
 29 23  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  6
 11 45  1  1
 14 46  1  0
 16 47  1  0
 21 48  1  0
 24 49  1  0
 25 50  1  0
 27 51  1  0
 28 52  1  0
 29 53  1  0
 32 54  1  0
 33 55  1  6
 34 56  1  0
 35 57  1  1
 36 58  1  0
 37 59  1  1
 38 60  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.334  -4.377   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.837   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -2.067   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.837   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -4.377   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -5.147   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -6.687   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -5.147   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -6.687   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -4.377   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.837   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -2.067   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -2.067   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.837   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -2.067   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.527   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   0.243   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -0.527   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336   0.243   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -5.147   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667  -2.067   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667   0.601   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.437   1.934   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.977   1.934   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.747   0.601   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.977  -0.733   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.437  -0.733   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.747  -2.067   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -7.287   0.601   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.747   3.268   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.667   3.268   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.437   4.602   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.667   5.935   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.437   7.269   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667   8.603   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -3.437   9.936   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -1.127   5.935   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -1.127   8.603   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   20                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    4                                                       
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16                                                            
CONECT   20   10                                                            
CONECT   21    2   27                                                       
CONECT   22   23   27                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   21   26   22                                                  
CONECT   28   26                                                            
CONECT   29   25                                                            
CONECT   30   24                                                            
CONECT   31   23   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35                                                            
CONECT   37   33                                                            
CONECT   38   35                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

COMPND    HMDB0301863
HETATM    1  O1  UNL     1       9.891   0.251  -0.892  1.00  0.00           O  
HETATM    2  C1  UNL     1       8.694  -0.145  -0.984  1.00  0.00           C  
HETATM    3  O2  UNL     1       7.651   0.681  -0.546  1.00  0.00           O  
HETATM    4  C2  UNL     1       8.461  -1.483  -1.559  1.00  0.00           C  
HETATM    5  C3  UNL     1       7.020  -1.813  -1.605  1.00  0.00           C  
HETATM    6  O3  UNL     1       6.682  -2.930  -2.076  1.00  0.00           O  
HETATM    7  O4  UNL     1       6.024  -0.973  -1.163  1.00  0.00           O  
HETATM    8  C4  UNL     1       4.645  -1.317  -1.219  1.00  0.00           C  
HETATM    9  C5  UNL     1       3.800  -0.167  -0.650  1.00  0.00           C  
HETATM   10  O5  UNL     1       2.503  -0.543  -0.726  1.00  0.00           O  
HETATM   11  C6  UNL     1       1.714  -0.249   0.382  1.00  0.00           C  
HETATM   12  O6  UNL     1       0.402  -0.578   0.187  1.00  0.00           O  
HETATM   13  C7  UNL     1      -0.695   0.231   0.203  1.00  0.00           C  
HETATM   14  C8  UNL     1      -0.638   1.582   0.432  1.00  0.00           C  
HETATM   15  C9  UNL     1      -1.778   2.368   0.439  1.00  0.00           C  
HETATM   16  O7  UNL     1      -1.712   3.738   0.672  1.00  0.00           O  
HETATM   17  C10 UNL     1      -3.022   1.793   0.212  1.00  0.00           C  
HETATM   18  C11 UNL     1      -4.131   2.603   0.226  1.00  0.00           C  
HETATM   19  O8  UNL     1      -4.025   3.837   0.441  1.00  0.00           O  
HETATM   20  C12 UNL     1      -5.373   1.989  -0.008  1.00  0.00           C  
HETATM   21  O9  UNL     1      -6.467   2.810   0.011  1.00  0.00           O  
HETATM   22  C13 UNL     1      -5.420   0.640  -0.235  1.00  0.00           C  
HETATM   23  C14 UNL     1      -6.675  -0.069  -0.486  1.00  0.00           C  
HETATM   24  C15 UNL     1      -7.917   0.506  -0.525  1.00  0.00           C  
HETATM   25  C16 UNL     1      -9.085  -0.229  -0.771  1.00  0.00           C  
HETATM   26  C17 UNL     1      -8.953  -1.573  -0.978  1.00  0.00           C  
HETATM   27  O10 UNL     1     -10.096  -2.327  -1.224  1.00  0.00           O  
HETATM   28  C18 UNL     1      -7.711  -2.195  -0.947  1.00  0.00           C  
HETATM   29  C19 UNL     1      -6.613  -1.442  -0.706  1.00  0.00           C  
HETATM   30  O11 UNL     1      -4.299  -0.085  -0.235  1.00  0.00           O  
HETATM   31  C20 UNL     1      -3.123   0.439  -0.023  1.00  0.00           C  
HETATM   32  C21 UNL     1      -1.974  -0.288  -0.019  1.00  0.00           C  
HETATM   33  C22 UNL     1       2.370  -1.061   1.515  1.00  0.00           C  
HETATM   34  O12 UNL     1       1.527  -1.232   2.575  1.00  0.00           O  
HETATM   35  C23 UNL     1       3.584  -0.215   1.867  1.00  0.00           C  
HETATM   36  O13 UNL     1       4.364  -0.853   2.836  1.00  0.00           O  
HETATM   37  C24 UNL     1       4.351   0.192   0.669  1.00  0.00           C  
HETATM   38  O14 UNL     1       4.530   1.585   0.707  1.00  0.00           O  
HETATM   39  H1  UNL     1       7.880   1.378   0.156  1.00  0.00           H  
HETATM   40  H2  UNL     1       8.851  -1.453  -2.618  1.00  0.00           H  
HETATM   41  H3  UNL     1       9.012  -2.275  -0.976  1.00  0.00           H  
HETATM   42  H4  UNL     1       4.521  -2.211  -0.569  1.00  0.00           H  
HETATM   43  H5  UNL     1       4.366  -1.545  -2.249  1.00  0.00           H  
HETATM   44  H6  UNL     1       3.955   0.671  -1.395  1.00  0.00           H  
HETATM   45  H7  UNL     1       1.848   0.828   0.574  1.00  0.00           H  
HETATM   46  H8  UNL     1       0.314   2.070   0.614  1.00  0.00           H  
HETATM   47  H9  UNL     1      -0.827   4.174   0.839  1.00  0.00           H  
HETATM   48  H10 UNL     1      -6.441   3.788   0.175  1.00  0.00           H  
HETATM   49  H11 UNL     1      -8.034   1.551  -0.365  1.00  0.00           H  
HETATM   50  H12 UNL     1     -10.021   0.278  -0.787  1.00  0.00           H  
HETATM   51  H13 UNL     1     -10.593  -2.738  -0.425  1.00  0.00           H  
HETATM   52  H14 UNL     1      -7.689  -3.261  -1.120  1.00  0.00           H  
HETATM   53  H15 UNL     1      -5.653  -1.941  -0.685  1.00  0.00           H  
HETATM   54  H16 UNL     1      -2.054  -1.356  -0.204  1.00  0.00           H  
HETATM   55  H17 UNL     1       2.771  -2.022   1.102  1.00  0.00           H  
HETATM   56  H18 UNL     1       0.702  -1.658   2.262  1.00  0.00           H  
HETATM   57  H19 UNL     1       3.160   0.686   2.385  1.00  0.00           H  
HETATM   58  H20 UNL     1       4.942  -0.134   3.225  1.00  0.00           H  
HETATM   59  H21 UNL     1       5.399  -0.217   0.798  1.00  0.00           H  
HETATM   60  H22 UNL     1       5.089   1.911  -0.022  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   39
CONECT    4    5   40   41
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   42   43
CONECT    9   10   37   44
CONECT   10   11
CONECT   11   12   33   45
CONECT   12   13
CONECT   13   14   14   32
CONECT   14   15   46
CONECT   15   16   17   17
CONECT   16   47
CONECT   17   18   31
CONECT   18   19   19   20
CONECT   20   21   22   22
CONECT   21   48
CONECT   22   23   30
CONECT   23   24   24   29
CONECT   24   25   49
CONECT   25   26   26   50
CONECT   26   27   28
CONECT   27   51
CONECT   28   29   29   52
CONECT   29   53
CONECT   30   31
CONECT   31   32   32
CONECT   32   54
CONECT   33   34   35   55
CONECT   34   56
CONECT   35   36   37   57
CONECT   36   58
CONECT   37   38   59
CONECT   38   60
END

HMDB0301863
     RDKit          3D
Apigenin 7-(6''-malonylglucoside)
 60 63  0  0  0  0  0  0  0  0999 V2000
    9.8912    0.2505   -0.8921 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6940   -0.1452   -0.9838 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6505    0.6811   -0.5455 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4609   -1.4825   -1.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0198   -1.8132   -1.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6824   -2.9298   -2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0245   -0.9729   -1.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6455   -1.3171   -1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7996   -0.1667   -0.6501 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5034   -0.5434   -0.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7136   -0.2492    0.3815 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4021   -0.5782    0.1870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6952    0.2313    0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376    1.5822    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782    2.3680    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121    3.7380    0.6723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0220    1.7932    0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1313    2.6029    0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0247    3.8367    0.4412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3735    1.9892   -0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4675    2.8103    0.0106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4205    0.6401   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6751   -0.0694   -0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9173    0.5059   -0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0852   -0.2293   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9533   -1.5730   -0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0965   -2.3274   -1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7109   -2.1951   -0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6134   -1.4417   -0.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2995   -0.0847   -0.2347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1230    0.4386   -0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735   -0.2882   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702   -1.0613    1.5148 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5266   -1.2324    2.5748 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5837   -0.2146    1.8666 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3638   -0.8530    2.8359 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510    0.1918    0.6692 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5299    1.5848    0.7070 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8804    1.3779    0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8507   -1.4531   -2.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0118   -2.2753   -0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208   -2.2105   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662   -1.5453   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9547    0.6709   -1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8478    0.8278    0.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3143    2.0705    0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8273    4.1742    0.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4409    3.7876    0.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0342    1.5510   -0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0211    0.2785   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5929   -2.7383   -0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6885   -3.2608   -1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6532   -1.9415   -0.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0536   -1.3562   -0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7707   -2.0216    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -1.6576    2.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1603    0.6857    2.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9420   -0.1343    3.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3988   -0.2174    0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0889    1.9114   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 22 30  1  0
 30 31  1  0
 31 32  2  0
 11 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37  9  1  0
 32 13  1  0
 31 17  1  0
 29 23  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  6
 11 45  1  1
 14 46  1  0
 16 47  1  0
 21 48  1  0
 24 49  1  0
 25 50  1  0
 27 51  1  0
 28 52  1  0
 29 53  1  0
 32 54  1  0
 33 55  1  6
 34 56  1  0
 35 57  1  1
 36 58  1  0
 37 59  1  1
 38 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-{[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3-oxopropanoate	Generator

Chemical Formula

C₂₄H₂₂O₁₄

Average Molecular Weight

534.4231

Monoisotopic Molecular Weight

534.100955412

IUPAC Name

3-{[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3-oxopropanoic acid

Traditional Name

3-{[(2R,3S,4S,5R,6S)-6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](O)[C@@H](COC(=O)CC(O)=O)O[C@@H](OC2=CC(O)=C3C(OC(=C(O)C3=O)C3=CC=C(O)C=C3)=C2)[C@@H]1O

InChI Identifier

InChI=1S/C24H22O14/c25-10-3-1-9(2-4-10)23-21(33)19(31)17-12(26)5-11(6-13(17)37-23)36-24-22(34)20(32)18(30)14(38-24)8-35-16(29)7-15(27)28/h1-6,14,18,20,22,24-26,30,32-34H,7-8H2,(H,27,28)/t14-,18-,20+,22-,24-/m1/s1

InChI Key

FIVFPODHFQLHTO-ZQIGZIPLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glucuronides

Alternative Parents

Substituents

Flavonoid-4p-o-glucuronide
3p-methoxyflavonoid-skeleton
3-methoxyflavonoid-skeleton
Hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
1-o-glucuronide
O-glucuronide
3-methoxychromone
Glucuronic acid or derivatives
O-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
Benzodioxole
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Beta-hydroxy acid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Hydroxy acid
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Polyol
Oxacycle
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Parsley (FooDB: FOOD00131)
German camomile (FooDB: FOOD00107)

Pulse

Other pulse

Lupine (FooDB: FOOD00104)

Process

Not Available

Role

Not Available

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
logP	1.03	ALOGPS
logP	0.53	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	229.74 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	122.52 m³·mol⁻¹	ChemAxon
Polarizability	49.88 Å³	ChemAxon
Number of Rings	4	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
AllCCS	[M+H]+	216.455	32859911
AllCCS	[M+H-H2O]+	214.749	32859911
AllCCS	[M+Na]+	218.446	32859911
AllCCS	[M+NH4]+	218.006	32859911
AllCCS	[M-H]-	214.012	32859911
AllCCS	[M+Na-2H]-	215.257	32859911
AllCCS	[M+HCOO]-	216.776	32859911
DeepCCS	[M+H]+	220.524	30932474
DeepCCS	[M-H]-	218.276	30932474
DeepCCS	[M-2H]-	251.594	30932474
DeepCCS	[M+Na]+	226.437	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-(6''-malonylglucoside) 10V, Positive-QTOF	splash10-000i-2090450000-09c25e983f8c9e5e34e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-(6''-malonylglucoside) 20V, Positive-QTOF	splash10-000i-1090100000-55ce70eecb5aa280c3b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-(6''-malonylglucoside) 40V, Positive-QTOF	splash10-00kr-3490000000-c8b93231fc0143a9e5d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-(6''-malonylglucoside) 10V, Negative-QTOF	splash10-0f8i-9770650000-99b99e49e5ecad6ccbca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-(6''-malonylglucoside) 20V, Negative-QTOF	splash10-0f79-7690200000-98b286c5a92187baa5a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-(6''-malonylglucoside) 40V, Negative-QTOF	splash10-0f80-5690000000-00fb976836807534c55f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-(6''-malonylglucoside) 10V, Negative-QTOF	splash10-001i-0000090000-5b2589fb398d24ef71b0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-(6''-malonylglucoside) 20V, Negative-QTOF	splash10-001i-0003190000-b1341df28350c3f5f14e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-(6''-malonylglucoside) 40V, Negative-QTOF	splash10-0fyy-4309230000-ea984984c35e74d703f0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-(6''-malonylglucoside) 10V, Positive-QTOF	splash10-000i-0000090000-1ab87d91566297c637a0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-(6''-malonylglucoside) 20V, Positive-QTOF	splash10-000i-0000090000-08481d313cdaaa31386c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-(6''-malonylglucoside) 40V, Positive-QTOF	splash10-0uy0-2001950000-1f255a02d9551c9ef8c6	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

FooDB ID

FDB001540

KNApSAcK ID

Not Available

Chemspider ID

59696195

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

145864962

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

Not Available

Showing metabocard for Apigenin 7-(6''-malonylglucoside) (HMDB0301863)

MOL for HMDB0301863 (Apigenin 7-(6''-malonylglucoside))

3D MOL for HMDB0301863 (Apigenin 7-(6''-malonylglucoside))

3D SDF for HMDB0301863 (Apigenin 7-(6''-malonylglucoside))

3D-SDF for HMDB0301863 (Apigenin 7-(6''-malonylglucoside))

PDB for HMDB0301863 (Apigenin 7-(6''-malonylglucoside))

3D PDB for HMDB0301863 (Apigenin 7-(6''-malonylglucoside))

SMILES for HMDB0301863 (Apigenin 7-(6''-malonylglucoside))

INCHI for HMDB0301863 (Apigenin 7-(6''-malonylglucoside))

Structure for HMDB0301863 (Apigenin 7-(6''-malonylglucoside))

3D Structure for HMDB0301863 (Apigenin 7-(6''-malonylglucoside))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra