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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 01:25:31 UTC

Update Date

2021-09-24 01:25:31 UTC

HMDB ID

HMDB0303375

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8-Hydroxygenistein

Description

8-hydroxygenistein is a member of the class of compounds known as isoflavones. Isoflavones are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. 8-hydroxygenistein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 8-hydroxygenistein can be found in a number of food items such as scarlet bean, mung bean, lima bean, and adzuki bean, which makes 8-hydroxygenistein a potential biomarker for the consumption of these food products.

Structure

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

HMDB0303375
     RDKit          3D
8-Hydroxygenistein
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.1520   -0.1659    1.7571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2988   -0.0446    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5701   -0.0392   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0120   -0.1758   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4600   -1.1259    0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8130   -1.2630    0.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6769   -0.4185    0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0362   -0.5608    0.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2252    0.5344   -0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701    0.6725   -0.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0534    0.0944   -1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2321    0.2162   -1.9806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0776    0.2139   -0.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4523    0.3413   -1.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9316    0.4748   -2.4914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3596    0.3425   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7278    0.4684   -0.3443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8728    0.2100    1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5166    0.0813    1.3705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0188   -0.0535    2.6782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6446    0.0850    0.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7401   -1.7744    1.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1603   -2.0183    1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7345    0.0041    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9047    1.1919   -1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167    1.4257   -1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779    0.0943   -2.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2848    0.4777   -3.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0571    0.5638   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5470    0.2030    2.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6813   -0.0551    3.4596 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
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 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
 15 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
M  END

  Mrv0541 02241214542D          

 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
   -1.4602    1.0089    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
  4 20  1  0  0  0  0
  7 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303375

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
ZKZCRGBCWBCSNJ-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.2363

> <EXACT_MASS>
286.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
27.5058818182405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7,8-trihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.773307068

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.907696923105078

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.787753701207648

> <JCHEM_PKA_STRONGEST_BASIC>
-5.100844376259972

> <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>
5,7,8-trihydroxy-3-(4-hydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303375
     RDKit          3D
8-Hydroxygenistein
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.1520   -0.1659    1.7571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2988   -0.0446    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5701   -0.0392   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0120   -0.1758   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4600   -1.1259    0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8130   -1.2630    0.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6769   -0.4185    0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0362   -0.5608    0.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2252    0.5344   -0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701    0.6725   -0.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0534    0.0944   -1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2321    0.2162   -1.9806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0776    0.2139   -0.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4523    0.3413   -1.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9316    0.4748   -2.4914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3596    0.3425   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7278    0.4684   -0.3443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8728    0.2100    1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5166    0.0813    1.3705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0188   -0.0535    2.6782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6446    0.0850    0.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7401   -1.7744    1.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1603   -2.0183    1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7345    0.0041    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9047    1.1919   -1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167    1.4257   -1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779    0.0943   -2.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2848    0.4777   -3.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0571    0.5638   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5470    0.2030    2.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6813   -0.0551    3.4596 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
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 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
 15 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  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      -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      -2.726   1.883   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                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   20                                                  
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    4                                                            
CONECT   21    7                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0303375
HETATM    1  O1  UNL     1       0.152  -0.166   1.757  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.299  -0.045   0.583  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.570  -0.039  -0.487  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.012  -0.176  -0.236  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.460  -1.126   0.649  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.813  -1.263   0.893  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.677  -0.418   0.219  1.00  0.00           C  
HETATM    8  O2  UNL     1       6.036  -0.561   0.467  1.00  0.00           O  
HETATM    9  C7  UNL     1       4.225   0.534  -0.669  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.870   0.672  -0.914  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.053   0.094  -1.757  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.232   0.216  -1.981  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.078   0.214  -0.980  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.452   0.341  -1.181  1.00  0.00           C  
HETATM   15  O4  UNL     1      -3.932   0.475  -2.491  1.00  0.00           O  
HETATM   16  C12 UNL     1      -4.360   0.342  -0.157  1.00  0.00           C  
HETATM   17  O5  UNL     1      -5.728   0.468  -0.344  1.00  0.00           O  
HETATM   18  C13 UNL     1      -3.873   0.210   1.131  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.517   0.081   1.371  1.00  0.00           C  
HETATM   20  O6  UNL     1      -2.019  -0.053   2.678  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.645   0.085   0.319  1.00  0.00           C  
HETATM   22  H1  UNL     1       1.740  -1.774   1.162  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.160  -2.018   1.596  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.734   0.004   0.027  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.905   1.192  -1.193  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.517   1.426  -1.616  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.778   0.094  -2.586  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.285   0.478  -3.273  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.057   0.564  -1.297  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.547   0.203   2.001  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.681  -0.055   3.460  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   16
CONECT   15   28
CONECT   16   17   18   18
CONECT   17   29
CONECT   18   19   30
CONECT   19   20   21   21
CONECT   20   31
END

HMDB0303375
     RDKit          3D
8-Hydroxygenistein
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.1520   -0.1659    1.7571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2988   -0.0446    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5701   -0.0392   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0120   -0.1758   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4600   -1.1259    0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8130   -1.2630    0.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6769   -0.4185    0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0362   -0.5608    0.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2252    0.5344   -0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701    0.6725   -0.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0534    0.0944   -1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2321    0.2162   -1.9806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0776    0.2139   -0.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4523    0.3413   -1.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9316    0.4748   -2.4914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3596    0.3425   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7278    0.4684   -0.3443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8728    0.2100    1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5166    0.0813    1.3705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0188   -0.0535    2.6782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6446    0.0850    0.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7401   -1.7744    1.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1603   -2.0183    1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7345    0.0041    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9047    1.1919   -1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167    1.4257   -1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779    0.0943   -2.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2848    0.4777   -3.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0571    0.5638   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5470    0.2030    2.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6813   -0.0551    3.4596 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
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 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
 15 28  1  0
 17 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

5,7,8-trihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

5,7,8-trihydroxy-3-(4-hydroxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

ZKZCRGBCWBCSNJ-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0303375)

Not Available

EC 2.1.1.6 (catechol O-methyltransferase) inhibitor (HMDB: HMDB0303375)

Phytoalexin (HMDB: HMDB0303375)

Industrial application

Agriculture

Pesticide (HMDB: HMDB0303375)

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	2.68	ALOGPS
logP	2.77	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.79	ChemAxon
pKa (Strongest Basic)	-5.1	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	27.51 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
AllCCS	[M+H]+	164.267	32859911
AllCCS	[M+H-H2O]+	160.496	32859911
AllCCS	[M+Na]+	168.776	32859911
AllCCS	[M+NH4]+	167.769	32859911
AllCCS	[M-H]-	163.536	32859911
AllCCS	[M+Na-2H]-	162.703	32859911
AllCCS	[M+HCOO]-	161.919	32859911
DeepCCS	[M+H]+	163.16	30932474
DeepCCS	[M-H]-	160.802	30932474
DeepCCS	[M-2H]-	193.688	30932474
DeepCCS	[M+Na]+	169.253	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 - 8-Hydroxygenistein 10V, Positive-QTOF	splash10-000i-0090000000-adc189b8bf74cddc783b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxygenistein 20V, Positive-QTOF	splash10-000i-1090000000-2322b06886c69afdea71	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxygenistein 40V, Positive-QTOF	splash10-014j-9860000000-4fc8d65cf8c987a3efba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxygenistein 10V, Negative-QTOF	splash10-000i-0090000000-8a897aee55c787a49452	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxygenistein 20V, Negative-QTOF	splash10-000i-0190000000-fa75e4d164bef7f32738	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxygenistein 40V, Negative-QTOF	splash10-0006-5930000000-9444e825b1398336ea1c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxygenistein 10V, Positive-QTOF	splash10-000i-0090000000-ad6070afb384abda8f3b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxygenistein 20V, Positive-QTOF	splash10-000i-0090000000-729519815713f93408c4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxygenistein 40V, Positive-QTOF	splash10-067l-0590000000-a3d07c68527d75215203	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxygenistein 10V, Negative-QTOF	splash10-000i-0090000000-3713e1ac18e8a67ad454	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxygenistein 20V, Negative-QTOF	splash10-000i-0190000000-16a410866b128e56bea6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxygenistein 40V, Negative-QTOF	splash10-000i-1920000000-e3c669b4718b7f829787	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

FDB012252

KNApSAcK ID

C00018071

Chemspider ID

4591233

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 8-Hydroxygenistein (HMDB0303375)

MOL for HMDB0303375 (8-Hydroxygenistein)

3D MOL for HMDB0303375 (8-Hydroxygenistein)

3D SDF for HMDB0303375 (8-Hydroxygenistein)

3D-SDF for HMDB0303375 (8-Hydroxygenistein)

PDB for HMDB0303375 (8-Hydroxygenistein)

3D PDB for HMDB0303375 (8-Hydroxygenistein)

SMILES for HMDB0303375 (8-Hydroxygenistein)

INCHI for HMDB0303375 (8-Hydroxygenistein)

Structure for HMDB0303375 (8-Hydroxygenistein)

3D Structure for HMDB0303375 (8-Hydroxygenistein)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra