Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Show more...Show more...Show more...

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:36:27 UTC

Update Date

2022-03-07 02:57:08 UTC

HMDB ID

HMDB0041688

Secondary Accession Numbers

HMDB41688

Metabolite Identification

Common Name

5,6,7,4'-Tetrahydroxyisoflavone

Description

5,6,7,4'-Tetrahydroxyisoflavone belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, 5,6,7,4'-tetrahydroxyisoflavone is considered to be a flavonoid. Based on a literature review very few articles have been published on 5,6,7,4'-Tetrahydroxyisoflavone.

Structure

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

HMDB0041688
     RDKit          3D
5,6,7,4'-Tetrahydroxyisoflavone
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.1400    1.1144    1.3710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155    0.2869    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6927   -0.4810   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1064   -0.3209    0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0556   -0.2303   -0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3873   -0.0787   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7709   -0.0177    0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344    0.1377    1.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8208   -0.1086    1.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4914   -0.2598    1.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112   -1.3782   -1.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694   -1.5104   -1.3753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9424   -0.7730   -0.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3070   -0.9017   -0.9534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240   -0.1381   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5949   -0.2775   -0.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8352    0.7788    0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7545    1.5597    1.4016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4828    0.9109    0.9422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0517    1.8318    1.9064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5613    0.1448    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7160   -0.2822   -1.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1438   -0.0061   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4777    1.0804    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1562   -0.0571    2.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662   -0.3283    2.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9802   -1.9565   -1.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6204   -1.6257   -1.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9575   -0.9185   -1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7294    1.4160    1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7046    2.3886    2.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  2  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
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 10  4  1  0
 21 13  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 16 29  1  0
 18 30  1  0
 20 31  1  0
M  END

  Mrv0541 02271201322D          

 21 23  0  0  0  0            999 V2000
   -2.1747   -1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1747   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891    0.1839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602    0.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7457   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7457   -1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602   -1.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -2.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -1.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832   -1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313    0.1839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1122   -2.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8266   -2.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8266   -1.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1122   -1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3977   -1.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3977   -2.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411   -2.7036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891   -1.4661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602   -2.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 17  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 14 19  1  0  0  0  0
  1 20  1  0  0  0  0
  7 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041688

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1=COC2=CC(O)=C(O)C(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)9-6-21-11-5-10(17)14(19)15(20)12(11)13(9)18/h1-6,16-17,19-20H

> <INCHI_KEY>
HDXSEWOOSVMREY-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.2363

> <EXACT_MASS>
286.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
27.503183051825673

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6,7-trihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.773307068

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.833865246191737

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.777318094918948

> <JCHEM_PKA_STRONGEST_BASIC>
-5.330926486167626

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
73.66380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxygenistein

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041688
     RDKit          3D
5,6,7,4'-Tetrahydroxyisoflavone
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.1400    1.1144    1.3710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155    0.2869    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6927   -0.4810   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1064   -0.3209    0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0556   -0.2303   -0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3873   -0.0787   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7709   -0.0177    0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344    0.1377    1.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8208   -0.1086    1.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4914   -0.2598    1.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112   -1.3782   -1.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694   -1.5104   -1.3753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9424   -0.7730   -0.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3070   -0.9017   -0.9534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240   -0.1381   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5949   -0.2775   -0.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8352    0.7788    0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7545    1.5597    1.4016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4828    0.9109    0.9422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0517    1.8318    1.9064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5613    0.1448    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7160   -0.2822   -1.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1438   -0.0061   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4777    1.0804    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1562   -0.0571    2.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662   -0.3283    2.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9802   -1.9565   -1.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6204   -1.6257   -1.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9575   -0.9185   -1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7294    1.4160    1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7046    2.3886    2.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  2  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
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 10  4  1  0
 21 13  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 16 29  1  0
 18 30  1  0
 20 31  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.059  -1.967   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.059  -0.427   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.393   0.343   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.726   0.343   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.392  -0.427   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.392  -1.967   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.726  -2.737   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.058  -4.277   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.058  -2.737   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.275  -1.967   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.275  -0.427   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.058   0.343   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.943  -5.047   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.276  -4.277   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.276  -2.737   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.943  -1.967   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.609  -2.737   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.609  -4.277   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.610  -5.047   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.393  -2.737   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.726  -4.277   0.000  0.00  0.00           O+0
CONECT    1    2    7   20                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    9                                                  
CONECT    7    1    6   21                                                  
CONECT    8    9                                                            
CONECT    9    6    8   10                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12    5   11                                                       
CONECT   13   14   18                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   10   16   18                                                  
CONECT   18   13   17                                                       
CONECT   19   14                                                            
CONECT   20    1                                                            
CONECT   21    7                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0041688
HETATM    1  O1  UNL     1       0.140   1.114   1.371  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.216   0.287   0.507  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.693  -0.481  -0.188  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.106  -0.321   0.094  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.056  -0.230  -0.918  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.387  -0.079  -0.595  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.771  -0.018   0.726  1.00  0.00           C  
HETATM    8  O2  UNL     1       6.134   0.138   1.068  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.821  -0.109   1.718  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.491  -0.260   1.412  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.211  -1.378  -1.133  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.069  -1.510  -1.375  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.942  -0.773  -0.707  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.307  -0.902  -0.953  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.224  -0.138  -0.263  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.595  -0.278  -0.520  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.835   0.779   0.694  1.00  0.00           C  
HETATM   18  O5  UNL     1      -4.755   1.560   1.402  1.00  0.00           O  
HETATM   19  C14 UNL     1      -2.483   0.911   0.942  1.00  0.00           C  
HETATM   20  O6  UNL     1      -2.052   1.832   1.906  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.561   0.145   0.249  1.00  0.00           C  
HETATM   22  H1  UNL     1       2.716  -0.282  -1.944  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.144  -0.006  -1.372  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.478   1.080   1.167  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.156  -0.057   2.749  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.766  -0.328   2.230  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.980  -1.956  -1.650  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.620  -1.626  -1.709  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.958  -0.918  -1.196  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.729   1.416   1.174  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.705   2.389   2.411  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4   11   11
CONECT    4    5    5   10
CONECT    5    6   22
CONECT    6    7    7   23
CONECT    7    8    9
CONECT    8   24
CONECT    9   10   10   25
CONECT   10   26
CONECT   11   12   27
CONECT   12   13
CONECT   13   14   14   21
CONECT   14   15   28
CONECT   15   16   17   17
CONECT   16   29
CONECT   17   18   19
CONECT   18   30
CONECT   19   20   21   21
CONECT   20   31
END

HMDB0041688
     RDKit          3D
5,6,7,4'-Tetrahydroxyisoflavone
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.1400    1.1144    1.3710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155    0.2869    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6927   -0.4810   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1064   -0.3209    0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0556   -0.2303   -0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3873   -0.0787   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7709   -0.0177    0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344    0.1377    1.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8208   -0.1086    1.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4914   -0.2598    1.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112   -1.3782   -1.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694   -1.5104   -1.3753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9424   -0.7730   -0.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3070   -0.9017   -0.9534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240   -0.1381   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5949   -0.2775   -0.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8352    0.7788    0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7545    1.5597    1.4016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4828    0.9109    0.9422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0517    1.8318    1.9064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5613    0.1448    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7160   -0.2822   -1.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1438   -0.0061   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4777    1.0804    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1562   -0.0571    2.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662   -0.3283    2.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9802   -1.9565   -1.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6204   -1.6257   -1.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9575   -0.9185   -1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7294    1.4160    1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7046    2.3886    2.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  2  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
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 10  4  1  0
 21 13  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 16 29  1  0
 18 30  1  0
 20 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀O₆

Average Molecular Weight

286.2363

Monoisotopic Molecular Weight

286.047738052

IUPAC Name

5,6,7-trihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

6-hydroxygenistein

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1=COC2=CC(O)=C(O)C(O)=C2C1=O

InChI Identifier

InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)9-6-21-11-5-10(17)14(19)15(20)12(11)13(9)18/h1-6,16-17,19-20H

InChI Key

HDXSEWOOSVMREY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050386 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041688)
Cell membrane (HMDB: HMDB0041688)

Excreta

Biofluid or Excreta

Urine (PMID: 11410004)

Source

Exogenous

Exogenous (HMDB: HMDB0041688)

Food

Food (HMDB: HMDB0041688)

Endogenous

Plant

Plant (HMDB: HMDB0041688)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041688)

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	0.16 g/L	ALOGPS
logP	2.71	ALOGPS
logP	2.77	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.78	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.66 m³·mol⁻¹	ChemAxon
Polarizability	27.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	164.378	30932474
DeepCCS	[M-H]-	162.02	30932474
DeepCCS	[M-2H]-	194.906	30932474
DeepCCS	[M+Na]+	170.471	30932474
AllCCS	[M+H]+	164.3	32859911
AllCCS	[M+H-H2O]+	160.5	32859911
AllCCS	[M+NH4]+	167.8	32859911
AllCCS	[M+Na]+	168.8	32859911
AllCCS	[M-H]-	163.5	32859911
AllCCS	[M+Na-2H]-	162.7	32859911
AllCCS	[M+HCOO]-	161.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6,7,4'-Tetrahydroxyisoflavone	OC1=CC=C(C=C1)C1=COC2=CC(O)=C(O)C(O)=C2C1=O	4345.7	Standard polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone	OC1=CC=C(C=C1)C1=COC2=CC(O)=C(O)C(O)=C2C1=O	2982.1	Standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone	OC1=CC=C(C=C1)C1=COC2=CC(O)=C(O)C(O)=C2C1=O	3043.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,6,7,4'-Tetrahydroxyisoflavone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=C(O)C(O)=C3C2=O)C=C1	3266.9	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C(O)=C1O)C(=O)C(C1=CC=C(O)C=C1)=CO2	3240.4	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,1TMS,isomer #3	C[Si](C)(C)OC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3)C(=O)C2=C1O	3127.9	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,1TMS,isomer #4	C[Si](C)(C)OC1=C(O)C(O)=CC2=C1C(=O)C(C1=CC=C(O)C=C1)=CO2	3169.1	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=C(O)C(O)=C3C2=O)C=C1	3156.7	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=C(O[Si](C)(C)C)C(O)=C3C2=O)C=C1	3142.7	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=C(O)C(O[Si](C)(C)C)=C3C2=O)C=C1	3070.1	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,2TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1O)C(=O)C(C1=CC=C(O)C=C1)=CO2	3123.5	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,2TMS,isomer #5	C[Si](C)(C)OC1=CC2=C(C(O)=C1O[Si](C)(C)C)C(=O)C(C1=CC=C(O)C=C1)=CO2	3093.2	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,2TMS,isomer #6	C[Si](C)(C)OC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3)C(=O)C2=C1O[Si](C)(C)C	3057.4	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O)=C3C2=O)C=C1	3033.7	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C3C2=O)C=C1	3024.6	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3C2=O)C=C1	3001.1	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,3TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1O[Si](C)(C)C)C(=O)C(C1=CC=C(O)C=C1)=CO2	3012.8	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3C2=O)C=C1	3007.2	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=C(O)C(O)=C3C2=O)C=C1	3526.6	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(O)=C1O)C(=O)C(C1=CC=C(O)C=C1)=CO2	3500.6	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3)C(=O)C2=C1O	3405.0	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=C(O)C(O)=CC2=C1C(=O)C(C1=CC=C(O)C=C1)=CO2	3451.6	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O)=C3C2=O)C=C1	3722.0	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C3C2=O)C=C1	3653.3	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1	3632.1	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O)C(=O)C(C1=CC=C(O)C=C1)=CO2	3680.8	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(O)=C1O[Si](C)(C)C(C)(C)C)C(=O)C(C1=CC=C(O)C=C1)=CO2	3638.4	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3635.7	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)=C3C2=O)C=C1	3820.8	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1	3815.2	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1	3764.8	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)C(=O)C(C1=CC=C(O)C=C1)=CO2	3748.4	Semi standard non polar	33892256
5,6,7,4'-Tetrahydroxyisoflavone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1	3926.0	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 - 5,6,7,4'-Tetrahydroxyisoflavone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0290000000-accc72ba0952d1f275fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone GC-MS (4 TMS) - 70eV, Positive	splash10-0mvi-2304190000-2e65d34c6d21388aba08	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - 5,6,7,4'-Tetrahydroxyisoflavone 10V, Positive-QTOF	splash10-000i-0090000000-80e7af47933f9ba9a0a4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone 20V, Positive-QTOF	splash10-000i-0090000000-8aa6019c77c38c07c9d8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone 40V, Positive-QTOF	splash10-02t9-5980000000-cd86ec93f68081be7baf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone 10V, Negative-QTOF	splash10-000i-0090000000-d7b532cfa4b615971d84	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone 20V, Negative-QTOF	splash10-000i-0090000000-07912bb4efe9be94a4fa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone 40V, Negative-QTOF	splash10-0avl-3940000000-3f97ecb56c6b92922bdb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone 10V, Positive-QTOF	splash10-000i-0090000000-ad6070afb384abda8f3b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone 20V, Positive-QTOF	splash10-000i-0090000000-6bc892fc37e7ffe0032a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone 40V, Positive-QTOF	splash10-0a4i-0490000000-5dc8cbe950c9c1311f74	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone 10V, Negative-QTOF	splash10-000i-0090000000-3713e1ac18e8a67ad454	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone 20V, Negative-QTOF	splash10-000i-0090000000-14b67f3a0a2523088978	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,4'-Tetrahydroxyisoflavone 40V, Negative-QTOF	splash10-00n0-1960000000-1f6c8398b96d21c801d5	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 840	11410004	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029849

KNApSAcK ID

C00009454

Chemspider ID

4795341

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6063386

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

Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

5,6,7,4'-Tetrahydroxyisoflavone → 3,4,5-trihydroxy-6-[4-(5,6,7-trihydroxy-4-oxo-4H-chromen-3-yl)phenoxy]oxane-2-carboxylic acid	details
5,6,7,4'-Tetrahydroxyisoflavone → 6-{[5,6-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

5,6,7,4'-Tetrahydroxyisoflavone → [4-(5,6,7-trihydroxy-4-oxo-4H-chromen-3-yl)phenyl]oxidanesulfonic acid	details

Showing metabocard for 5,6,7,4'-Tetrahydroxyisoflavone (HMDB0041688)

MOL for HMDB0041688 (5,6,7,4'-Tetrahydroxyisoflavone)

3D MOL for HMDB0041688 (5,6,7,4'-Tetrahydroxyisoflavone)

3D SDF for HMDB0041688 (5,6,7,4'-Tetrahydroxyisoflavone)

3D-SDF for HMDB0041688 (5,6,7,4'-Tetrahydroxyisoflavone)

PDB for HMDB0041688 (5,6,7,4'-Tetrahydroxyisoflavone)

3D PDB for HMDB0041688 (5,6,7,4'-Tetrahydroxyisoflavone)

SMILES for HMDB0041688 (5,6,7,4'-Tetrahydroxyisoflavone)

INCHI for HMDB0041688 (5,6,7,4'-Tetrahydroxyisoflavone)

Structure for HMDB0041688 (5,6,7,4'-Tetrahydroxyisoflavone)

3D Structure for HMDB0041688 (5,6,7,4'-Tetrahydroxyisoflavone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions