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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:41:04 UTC

Update Date

2022-03-07 02:55:19 UTC

HMDB ID

HMDB0037435

Secondary Accession Numbers

HMDB37435

Metabolite Identification

Common Name

2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin

Description

2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin, also known as KDCG or kaempferol-2,4-dicoumaroyl-3-O-glucoside, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, fats and oils, and robusta coffees (Coffea canephora). This could make 2'',4''-bis-O-(4-hydroxycinnamoyl)astragalin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin.

Structure

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


  Mrv0541 02241220072D          

 54 59  0  0  0  0            999 V2000
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 52 53  2  0  0  0  0
M  END

HMDB0037435
     RDKit          3D
2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin
 86 91  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 02241220072D          

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  1  2  2  0  0  0  0
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  2  8  1  0  0  0  0
  3  4  2  0  0  0  0
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  4  5  1  0  0  0  0
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  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
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 39 40  2  0  0  0  0
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 41 42  2  0  0  0  0
 44 45  2  0  0  0  0
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 47 48  1  0  0  0  0
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 51 52  1  0  0  0  0
 51 54  1  0  0  0  0
 52 53  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037435

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(OC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C1OC(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C39H32O15/c40-19-29-36(52-30(46)15-5-20-1-9-23(41)10-2-20)34(49)38(53-31(47)16-6-21-3-11-24(42)12-4-21)39(51-29)54-37-33(48)32-27(45)17-26(44)18-28(32)50-35(37)22-7-13-25(43)14-8-22/h1-18,29,34,36,38-45,49H,19H2/b15-5+,16-6+

> <INCHI_KEY>
FVUOCOCBVMNVGQ-IAGONARPSA-N

> <FORMULA>
C39H32O15

> <MOLECULAR_WEIGHT>
740.6624

> <EXACT_MASS>
740.174120354

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
73.1480253861679

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-4-hydroxy-6-(hydroxymethyl)-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
4.39

> <JCHEM_LOGP>
5.619380818333333

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.35474790895588

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.432946645389337

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9818171730060197

> <JCHEM_POLAR_SURFACE_AREA>
238.96999999999997

> <JCHEM_REFRACTIVITY>
190.39179999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-4-hydroxy-6-(hydroxymethyl)-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037435
     RDKit          3D
2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin
 86 91  0  0  0  0  0  0  0  0999 V2000
    4.6684   -0.9452   -2.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7274   -1.2082   -0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0312   -1.3969   -0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1741   -1.7068    0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13 14  1  0
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 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 21 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
 37 38  1  0
 38 39  2  0
 18 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  2  0
 42 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 47 48  1  0
 48 49  2  0
 49 50  1  0
 49 51  1  0
 51 52  2  0
 40 53  1  0
 53 54  1  0
 11  5  1  0
 53 13  1  0
 38 20  1  0
 52 46  1  0
 28 22  1  0
 37 30  1  0
  3 55  1  0
  4 56  1  0
  6 57  1  0
  7 58  1  0
  9 59  1  0
 10 60  1  0
 11 61  1  0
 13 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 18 67  1  0
 23 68  1  0
 24 69  1  0
 26 70  1  0
 27 71  1  0
 28 72  1  0
 31 73  1  0
 33 74  1  0
 34 75  1  0
 36 76  1  0
 40 77  1  0
 44 78  1  0
 45 79  1  0
 47 80  1  0
 48 81  1  0
 50 82  1  0
 51 83  1  0
 52 84  1  0
 53 85  1  0
 54 86  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  O   UNK     0      -4.668  -3.465   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.668  -5.005   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.334  -5.775   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.334  -7.315   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.668  -8.084   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -7.335  -3.465   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -7.335  -5.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.000  -5.775   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.000  -7.315   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.335  -8.084   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.670  -5.775   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.670  -7.315   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -10.002  -8.084   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.667  -8.084   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.667  -7.315   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.002  -8.084   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.002  -9.624   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.667 -10.394   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.667  -9.624   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.999 -10.394   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.002  -5.005   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.002  -3.465   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.334  -2.695   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.334  -1.155   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.668  -0.385   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.668   1.155   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.667  -3.465   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.667  -2.695   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.667  -1.155   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.667  -0.385   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.002  -0.385   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.002   1.155   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.667   1.155   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.667   1.925   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.667   3.465   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.667   4.235   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.667   5.775   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.667   6.544   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.667   8.084   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.667   8.854   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.999   8.084   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.999   6.544   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       0.667  10.394   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       1.999  -1.155   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       1.999  -2.695   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.334  -3.465   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.666  -2.695   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.000  -3.465   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       6.000  -5.005   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       7.335  -5.775   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       8.667  -5.005   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       8.667  -3.465   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       7.335  -2.695   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      10.002  -5.775   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    9                                                       
CONECT    6    7                                                            
CONECT    7    6    8   11                                                  
CONECT    8    2    7    9                                                  
CONECT    9    5    8   10                                                  
CONECT   10    9   12                                                       
CONECT   11    7   12                                                       
CONECT   12   10   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16    4   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   14   18   20                                                  
CONECT   20   19                                                            
CONECT   21    3   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   28   45                                                       
CONECT   28   22   27   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   24   29   32                                                  
CONECT   32   31   34                                                       
CONECT   33   34                                                            
CONECT   34   32   33   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   37   41                                                       
CONECT   43   40                                                            
CONECT   44   45                                                            
CONECT   45   27   44   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   53                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   54                                                  
CONECT   52   51   53                                                       
CONECT   53   48   52                                                       
CONECT   54   51                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  118    0
END

COMPND    HMDB0037435
HETATM    1  O1  UNL     1       4.668  -0.945  -2.225  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.727  -1.208  -0.993  1.00  0.00           C  
HETATM    3  C2  UNL     1       6.031  -1.397  -0.366  1.00  0.00           C  
HETATM    4  C3  UNL     1       6.174  -1.707   0.902  1.00  0.00           C  
HETATM    5  C4  UNL     1       7.445  -1.897   1.554  1.00  0.00           C  
HETATM    6  C5  UNL     1       7.425  -2.308   2.885  1.00  0.00           C  
HETATM    7  C6  UNL     1       8.619  -2.486   3.520  1.00  0.00           C  
HETATM    8  C7  UNL     1       9.842  -2.280   2.912  1.00  0.00           C  
HETATM    9  O2  UNL     1      11.027  -2.475   3.605  1.00  0.00           O  
HETATM   10  C8  UNL     1       9.825  -1.877   1.605  1.00  0.00           C  
HETATM   11  C9  UNL     1       8.631  -1.684   0.923  1.00  0.00           C  
HETATM   12  O3  UNL     1       3.570  -1.320  -0.231  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.319  -1.157  -0.844  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.384  -2.320  -0.662  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.944  -2.924  -1.969  1.00  0.00           C  
HETATM   16  O4  UNL     1       0.234  -4.081  -1.729  1.00  0.00           O  
HETATM   17  O5  UNL     1       0.333  -1.998   0.184  1.00  0.00           O  
HETATM   18  C13 UNL     1      -0.517  -1.000  -0.354  1.00  0.00           C  
HETATM   19  O6  UNL     1      -1.409  -1.700  -1.173  1.00  0.00           O  
HETATM   20  C14 UNL     1      -2.729  -1.937  -0.756  1.00  0.00           C  
HETATM   21  C15 UNL     1      -3.754  -1.165  -1.179  1.00  0.00           C  
HETATM   22  C16 UNL     1      -3.667  -0.035  -2.112  1.00  0.00           C  
HETATM   23  C17 UNL     1      -4.758   0.805  -2.222  1.00  0.00           C  
HETATM   24  C18 UNL     1      -4.819   1.855  -3.115  1.00  0.00           C  
HETATM   25  C19 UNL     1      -3.762   2.107  -3.953  1.00  0.00           C  
HETATM   26  O7  UNL     1      -3.795   3.170  -4.875  1.00  0.00           O  
HETATM   27  C20 UNL     1      -2.660   1.286  -3.866  1.00  0.00           C  
HETATM   28  C21 UNL     1      -2.624   0.225  -2.947  1.00  0.00           C  
HETATM   29  O8  UNL     1      -4.960  -1.477  -0.691  1.00  0.00           O  
HETATM   30  C22 UNL     1      -5.151  -2.456   0.132  1.00  0.00           C  
HETATM   31  C23 UNL     1      -6.436  -2.737   0.614  1.00  0.00           C  
HETATM   32  C24 UNL     1      -6.697  -3.762   1.492  1.00  0.00           C  
HETATM   33  O9  UNL     1      -7.974  -4.027   1.958  1.00  0.00           O  
HETATM   34  C25 UNL     1      -5.679  -4.575   1.945  1.00  0.00           C  
HETATM   35  C26 UNL     1      -4.407  -4.316   1.483  1.00  0.00           C  
HETATM   36  O10 UNL     1      -3.317  -5.101   1.899  1.00  0.00           O  
HETATM   37  C27 UNL     1      -4.140  -3.280   0.594  1.00  0.00           C  
HETATM   38  C28 UNL     1      -2.888  -3.007   0.130  1.00  0.00           C  
HETATM   39  O11 UNL     1      -1.901  -3.705   0.495  1.00  0.00           O  
HETATM   40  C29 UNL     1       0.213   0.158  -0.862  1.00  0.00           C  
HETATM   41  O12 UNL     1      -0.254   1.428  -0.492  1.00  0.00           O  
HETATM   42  C30 UNL     1      -0.338   2.452  -1.410  1.00  0.00           C  
HETATM   43  O13 UNL     1       0.038   2.216  -2.584  1.00  0.00           O  
HETATM   44  C31 UNL     1      -0.845   3.796  -1.079  1.00  0.00           C  
HETATM   45  C32 UNL     1      -1.236   4.050   0.135  1.00  0.00           C  
HETATM   46  C33 UNL     1      -1.749   5.349   0.537  1.00  0.00           C  
HETATM   47  C34 UNL     1      -2.122   5.551   1.869  1.00  0.00           C  
HETATM   48  C35 UNL     1      -2.615   6.736   2.321  1.00  0.00           C  
HETATM   49  C36 UNL     1      -2.762   7.778   1.470  1.00  0.00           C  
HETATM   50  O14 UNL     1      -3.257   8.998   1.872  1.00  0.00           O  
HETATM   51  C37 UNL     1      -2.401   7.625   0.119  1.00  0.00           C  
HETATM   52  C38 UNL     1      -1.902   6.409  -0.310  1.00  0.00           C  
HETATM   53  C39 UNL     1       1.690   0.131  -0.350  1.00  0.00           C  
HETATM   54  O15 UNL     1       1.733   0.287   1.016  1.00  0.00           O  
HETATM   55  H1  UNL     1       6.941  -1.275  -0.972  1.00  0.00           H  
HETATM   56  H2  UNL     1       5.230  -1.821   1.455  1.00  0.00           H  
HETATM   57  H3  UNL     1       6.495  -2.475   3.374  1.00  0.00           H  
HETATM   58  H4  UNL     1       8.648  -2.811   4.571  1.00  0.00           H  
HETATM   59  H5  UNL     1      11.064  -2.767   4.563  1.00  0.00           H  
HETATM   60  H6  UNL     1      10.766  -1.710   1.089  1.00  0.00           H  
HETATM   61  H7  UNL     1       8.698  -1.365  -0.094  1.00  0.00           H  
HETATM   62  H8  UNL     1       2.471  -1.018  -1.957  1.00  0.00           H  
HETATM   63  H9  UNL     1       1.958  -3.118  -0.127  1.00  0.00           H  
HETATM   64  H10 UNL     1       1.867  -3.232  -2.534  1.00  0.00           H  
HETATM   65  H11 UNL     1       0.427  -2.196  -2.627  1.00  0.00           H  
HETATM   66  H12 UNL     1       0.118  -4.644  -2.539  1.00  0.00           H  
HETATM   67  H13 UNL     1      -1.109  -0.658   0.541  1.00  0.00           H  
HETATM   68  H14 UNL     1      -5.604   0.605  -1.549  1.00  0.00           H  
HETATM   69  H15 UNL     1      -5.679   2.503  -3.180  1.00  0.00           H  
HETATM   70  H16 UNL     1      -4.174   2.970  -5.807  1.00  0.00           H  
HETATM   71  H17 UNL     1      -1.816   1.463  -4.515  1.00  0.00           H  
HETATM   72  H18 UNL     1      -1.740  -0.377  -2.941  1.00  0.00           H  
HETATM   73  H19 UNL     1      -7.235  -2.112   0.264  1.00  0.00           H  
HETATM   74  H20 UNL     1      -8.525  -4.674   1.408  1.00  0.00           H  
HETATM   75  H21 UNL     1      -5.836  -5.388   2.632  1.00  0.00           H  
HETATM   76  H22 UNL     1      -3.511  -5.849   2.551  1.00  0.00           H  
HETATM   77  H23 UNL     1       0.343   0.139  -1.958  1.00  0.00           H  
HETATM   78  H24 UNL     1      -0.880   4.550  -1.870  1.00  0.00           H  
HETATM   79  H25 UNL     1      -1.172   3.238   0.875  1.00  0.00           H  
HETATM   80  H26 UNL     1      -2.014   4.735   2.568  1.00  0.00           H  
HETATM   81  H27 UNL     1      -2.880   6.815   3.381  1.00  0.00           H  
HETATM   82  H28 UNL     1      -2.642   9.702   2.200  1.00  0.00           H  
HETATM   83  H29 UNL     1      -2.522   8.467  -0.564  1.00  0.00           H  
HETATM   84  H30 UNL     1      -1.630   6.316  -1.376  1.00  0.00           H  
HETATM   85  H31 UNL     1       2.183   0.971  -0.837  1.00  0.00           H  
HETATM   86  H32 UNL     1       2.412   0.950   1.263  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   55
CONECT    4    5   56
CONECT    5    6    6   11
CONECT    6    7   57
CONECT    7    8    8   58
CONECT    8    9   10
CONECT    9   59
CONECT   10   11   11   60
CONECT   11   61
CONECT   12   13
CONECT   13   14   53   62
CONECT   14   15   17   63
CONECT   15   16   64   65
CONECT   16   66
CONECT   17   18
CONECT   18   19   40   67
CONECT   19   20
CONECT   20   21   21   38
CONECT   21   22   29
CONECT   22   23   23   28
CONECT   23   24   68
CONECT   24   25   25   69
CONECT   25   26   27
CONECT   26   70
CONECT   27   28   28   71
CONECT   28   72
CONECT   29   30
CONECT   30   31   31   37
CONECT   31   32   73
CONECT   32   33   34   34
CONECT   33   74
CONECT   34   35   75
CONECT   35   36   37   37
CONECT   36   76
CONECT   37   38
CONECT   38   39   39
CONECT   40   41   53   77
CONECT   41   42
CONECT   42   43   43   44
CONECT   44   45   45   78
CONECT   45   46   79
CONECT   46   47   47   52
CONECT   47   48   80
CONECT   48   49   49   81
CONECT   49   50   51
CONECT   50   82
CONECT   51   52   52   83
CONECT   52   84
CONECT   53   54   85
CONECT   54   86
END

HMDB0037435
     RDKit          3D
2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin
 86 91  0  0  0  0  0  0  0  0999 V2000
    4.6684   -0.9452   -2.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7274   -1.2082   -0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0312   -1.3969   -0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1741   -1.7068    0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4454   -1.8972    1.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4248   -2.3082    2.8849 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6188   -2.4859    3.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8416   -2.2803    2.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0272   -2.4751    3.6046 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8250   -1.8774    1.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6314   -1.6844    0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698   -1.3203   -0.2312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3186   -1.1570   -0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838   -2.3197   -0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440   -2.9238   -1.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2342   -4.0805   -1.7295 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334   -1.9979    0.1843 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6148    6.7355    2.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7620    7.7784    1.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2572    8.9975    1.8723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4005    7.6253    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016    6.4091   -0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6896    0.1306   -0.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7331    0.2866    1.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6977   -1.3649   -0.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-4-hydroxy-6-(hydroxymethyl)-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid	HMDB
KDCG	HMDB
Kaempferol-2,4-dicoumaroyl-3-O-glucoside	HMDB
Astragalin-2'',4''-di-p-coumaroil	HMDB

Chemical Formula

C₃₉H₃₂O₁₅

Average Molecular Weight

740.6624

Monoisotopic Molecular Weight

740.174120354

IUPAC Name

2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-4-hydroxy-6-(hydroxymethyl)-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

2-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-4-hydroxy-6-(hydroxymethyl)-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

85122-24-3

SMILES

OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(OC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C1OC(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C39H32O15/c40-19-29-36(52-30(46)15-5-20-1-9-23(41)10-2-20)34(49)38(53-31(47)16-6-21-3-11-24(42)12-4-21)39(51-29)54-37-33(48)32-27(45)17-26(44)18-28(32)50-35(37)22-7-13-25(43)14-8-22/h1-18,29,34,36,38-45,49H,19H2/b15-5+,16-6+

InChI Key

FVUOCOCBVMNVGQ-IAGONARPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Flavone
Coumaric acid ester
Cinnamic acid ester
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Glycosyl compound
Chromone
O-glycosyl compound
1-benzopyran
Benzopyran
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Pyranone
Oxane
Benzenoid
Monocyclic benzene moiety
Monosaccharide
Fatty acyl
Pyran
Dicarboxylic acid or derivatives
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037435)

Cellular substructure

Membrane (HMDB: HMDB0037435)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037435)

Source

Exogenous

Food

Food (HMDB: HMDB0037435)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0037435)
Coffea (HMDB: HMDB0037435)

Not Available

Nutrient (HMDB: HMDB0037435)

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	0.029 g/L	ALOGPS
logP	4.39	ALOGPS
logP	5.62	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	238.97 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	190.39 m³·mol⁻¹	ChemAxon
Polarizability	73.15 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	257.669	30932474
DeepCCS	[M-H]-	256.016	30932474
DeepCCS	[M-2H]-	290.052	30932474
DeepCCS	[M+Na]+	263.826	30932474
AllCCS	[M+H]+	261.4	32859911
AllCCS	[M+H-H2O]+	260.9	32859911
AllCCS	[M+NH4]+	261.9	32859911
AllCCS	[M+Na]+	262.0	32859911
AllCCS	[M-H]-	246.8	32859911
AllCCS	[M+Na-2H]-	249.4	32859911
AllCCS	[M+HCOO]-	252.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin	OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(OC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C1OC(=O)\C=C\C1=CC=C(O)C=C1	9713.3	Standard polar	33892256
2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin	OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(OC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C1OC(=O)\C=C\C1=CC=C(O)C=C1	5996.0	Standard non polar	33892256
2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin	OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(OC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C1OC(=O)\C=C\C1=CC=C(O)C=C1	7363.9	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 - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (Non-derivatized) - 70eV, Positive	splash10-05rr-4460490200-9aa7545bacc22f27ea81	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin GC-MS (TMS_2_17) - 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 - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin 10V, Positive-QTOF	splash10-000j-0390150500-477c84cd00d469456bf3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin 20V, Positive-QTOF	splash10-000i-0290010000-2ad856db659be4532125	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin 40V, Positive-QTOF	splash10-000i-0390100000-e8a591e84ed16a8fa2e0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin 10V, Negative-QTOF	splash10-000i-0481290800-bb8155ae497362c4e292	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin 20V, Negative-QTOF	splash10-000i-0591120100-f0ccabd717690d7b105d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin 40V, Negative-QTOF	splash10-01p9-1960000000-7f1a2ac54183f78efc76	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin 10V, Negative-QTOF	splash10-000i-0000000900-09d6337c7ef74b9db0d8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin 20V, Negative-QTOF	splash10-000i-0050000900-4dc703e055f399392bc6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin 40V, Negative-QTOF	splash10-001r-0090000000-24406f2c09a244c142d3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin 10V, Positive-QTOF	splash10-000i-0090000200-cea8b7157671bdd54ac6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin 20V, Positive-QTOF	splash10-000o-0090000900-6b5e9683e395a902e200	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin 40V, Positive-QTOF	splash10-000i-0090000000-03ec6f5113b2bb58d5cf	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB016487

KNApSAcK ID

Not Available

Chemspider ID

4943050

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438582

PDB ID

Not Available

ChEBI ID

169547

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 2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin (HMDB0037435)

MOL for HMDB0037435 (2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin)

3D MOL for HMDB0037435 (2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin)

3D SDF for HMDB0037435 (2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin)

3D-SDF for HMDB0037435 (2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin)

PDB for HMDB0037435 (2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin)

3D PDB for HMDB0037435 (2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin)

SMILES for HMDB0037435 (2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin)

INCHI for HMDB0037435 (2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin)

Structure for HMDB0037435 (2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin)

3D Structure for HMDB0037435 (2'',4''-Bis-O-(4-hydroxycinnamoyl)astragalin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra