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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:34:36 UTC

Update Date

2022-03-07 02:57:07 UTC

HMDB ID

HMDB0041658

Secondary Accession Numbers

HMDB41658

Metabolite Identification

Common Name

3'-Hydroxygenistein

Description

3'-Hydroxygenistein, also known as isoluteolin or norsantal, 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, 3'-hydroxygenistein is considered to be a flavonoid. 3'-Hydroxygenistein is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 3'-Hydroxygenistein.

Structure

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

HMDB0041658
     RDKit          3D
3'-Hydroxygenistein
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.2473    0.3896    1.6619 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821    0.2686    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2568    0.1836   -0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650    0.2413   -0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203    1.1911    0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4607    1.2773    1.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3880    0.3894    0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7144    0.4988    0.8602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9440   -0.5559   -0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8097   -1.4497   -0.9586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895   -0.6288   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2229    0.0519   -1.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097    0.0081   -2.0422 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4118    0.0863   -1.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7703    0.0355   -1.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7218    0.1163   -0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0846    0.0593   -0.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3403    0.2503    0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757    0.3042    1.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6916    0.4368    2.5651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0364    0.2222    0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4485    1.9048    1.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8337    2.0152    1.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4220   -0.1102    0.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7848   -1.5076   -0.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3008   -1.3960   -1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5074   -0.0135   -2.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339   -0.0722   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5547   -0.8590   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1138    0.3105    1.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487    0.4950    3.0183 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  1  0
  9 11  2  0
  3 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 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
 11  4  1  0
 21 14  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
M  END


  Mrv0541 02271201292D          

 21 23  0  0  0  0            999 V2000
    4.5012   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7867   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7867   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0722   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3578   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3578   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0722   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6433   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6433   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2143   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5001    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9291    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5001   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5001   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2143   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5012   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 11 18  2  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041658

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C(O)=C1

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

> <INCHI_KEY>
IOYHCQBYQJQBSK-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.2363

> <EXACT_MASS>
286.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
27.53209482020776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.773307068

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.58096078715371

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.604244293063947

> <JCHEM_PKA_STRONGEST_BASIC>
-5.179055343026602

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
73.6638

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quercitin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041658
     RDKit          3D
3'-Hydroxygenistein
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.2473    0.3896    1.6619 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821    0.2686    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2568    0.1836   -0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650    0.2413   -0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203    1.1911    0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4607    1.2773    1.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3880    0.3894    0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7144    0.4988    0.8602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9440   -0.5559   -0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8097   -1.4497   -0.9586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895   -0.6288   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2229    0.0519   -1.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097    0.0081   -2.0422 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4118    0.0863   -1.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7703    0.0355   -1.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7218    0.1163   -0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0846    0.0593   -0.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3403    0.2503    0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757    0.3042    1.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6916    0.4368    2.5651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0364    0.2222    0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4485    1.9048    1.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8337    2.0152    1.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4220   -0.1102    0.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7848   -1.5076   -0.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3008   -1.3960   -1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5074   -0.0135   -2.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339   -0.0722   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5547   -0.8590   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1138    0.3105    1.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487    0.4950    3.0183 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  1  0
  9 11  2  0
  3 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 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
 11  4  1  0
 21 14  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
 17 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  O   UNK     0       8.402  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.069  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.069  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.735  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.401  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.401  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.735  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.067  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.067  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.734   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.400  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.934   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.267  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.601   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.267  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.934  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.934  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.400  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.734  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.734  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.402  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18    8   20                                                  
CONECT   20   19                                                            
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0041658
HETATM    1  O1  UNL     1       0.247   0.390   1.662  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.682   0.269   0.492  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.257   0.184  -0.543  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.665   0.241  -0.201  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.120   1.191   0.688  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.461   1.277   1.040  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.388   0.389   0.491  1.00  0.00           C  
HETATM    8  O2  UNL     1      -5.714   0.499   0.860  1.00  0.00           O  
HETATM    9  C7  UNL     1      -3.944  -0.556  -0.392  1.00  0.00           C  
HETATM   10  O3  UNL     1      -4.810  -1.450  -0.959  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.589  -0.629  -0.736  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.223   0.052  -1.813  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.510   0.008  -2.042  1.00  0.00           O  
HETATM   14  C10 UNL     1       2.412   0.086  -1.084  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.770   0.036  -1.373  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.722   0.116  -0.379  1.00  0.00           C  
HETATM   17  O5  UNL     1       6.085   0.059  -0.732  1.00  0.00           O  
HETATM   18  C13 UNL     1       4.340   0.250   0.932  1.00  0.00           C  
HETATM   19  C14 UNL     1       2.976   0.304   1.251  1.00  0.00           C  
HETATM   20  O6  UNL     1       2.692   0.437   2.565  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.036   0.222   0.248  1.00  0.00           C  
HETATM   22  H1  UNL     1      -1.448   1.905   1.144  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.834   2.015   1.735  1.00  0.00           H  
HETATM   24  H3  UNL     1      -6.422  -0.110   0.499  1.00  0.00           H  
HETATM   25  H4  UNL     1      -5.785  -1.508  -0.803  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.301  -1.396  -1.438  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.507  -0.014  -2.610  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.034  -0.072  -2.434  1.00  0.00           H  
HETATM   29  H8  UNL     1       6.555  -0.859  -0.770  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.114   0.310   1.683  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.849   0.495   3.018  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4   12   12
CONECT    4    5    5   11
CONECT    5    6   22
CONECT    6    7    7   23
CONECT    7    8    9
CONECT    8   24
CONECT    9   10   11   11
CONECT   10   25
CONECT   11   26
CONECT   12   13   27
CONECT   13   14
CONECT   14   15   15   21
CONECT   15   16   28
CONECT   16   17   18   18
CONECT   17   29
CONECT   18   19   30
CONECT   19   20   21   21
CONECT   20   31
END

HMDB0041658
     RDKit          3D
3'-Hydroxygenistein
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.2473    0.3896    1.6619 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821    0.2686    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2568    0.1836   -0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650    0.2413   -0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203    1.1911    0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4607    1.2773    1.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3880    0.3894    0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7144    0.4988    0.8602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9440   -0.5559   -0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8097   -1.4497   -0.9586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895   -0.6288   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2229    0.0519   -1.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097    0.0081   -2.0422 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4118    0.0863   -1.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7703    0.0355   -1.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7218    0.1163   -0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0846    0.0593   -0.7316 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3403    0.2503    0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757    0.3042    1.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6916    0.4368    2.5651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0364    0.2222    0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4485    1.9048    1.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8337    2.0152    1.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4220   -0.1102    0.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7848   -1.5076   -0.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3008   -1.3960   -1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5074   -0.0135   -2.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339   -0.0722   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5547   -0.8590   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1138    0.3105    1.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487    0.4950    3.0183 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  1  0
  9 11  2  0
  3 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 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
 11  4  1  0
 21 14  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 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

Value	Source
3',4',5,7-Tetrahydroxyisoflavone	ChEBI
5,7-Dihydroxy-3-(3,4-dihydroxyphenyl)-4-1H-benzopyran-4-one	ChEBI
Isoluteolin	ChEBI
Norsantal	ChEBI
Santol	ChEBI
3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one	HMDB
3'-Hydroxygenistein	ChEBI

Chemical Formula

C₁₅H₁₀O₆

Average Molecular Weight

286.2363

Monoisotopic Molecular Weight

286.047738052

IUPAC Name

3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

Traditional Name

quercitin

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C(O)=C1

InChI Identifier

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

InChI Key

IOYHCQBYQJQBSK-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
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:69437 )
isoflavones (C10510 )
Isoflavonoids (C10510 )
Isoflavonoids (LMPK12050251 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0041658)

Biofluid or Excreta

Urine (HMDB: HMDB0041658)

Excreta

Biofluid or Excreta

Urine (PMID: 15506819)

Cellular substructure

Membrane (HMDB: HMDB0041658)

Source

Exogenous

Food

Food (HMDB: HMDB0041658)

Endogenous

Plant

Plant (HMDB: HMDB0041658)

Not Available

Nutrient (HMDB: HMDB0041658)

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	0.14 g/L	ALOGPS
logP	2.64	ALOGPS
logP	2.77	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.6	ChemAxon
pKa (Strongest Basic)	-5.2	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	27.53 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]+	167.673	30932474
DeepCCS	[M-H]-	165.315	30932474
DeepCCS	[M-2H]-	198.802	30932474
DeepCCS	[M+Na]+	174.029	30932474
AllCCS	[M+H]+	164.5	32859911
AllCCS	[M+H-H2O]+	160.7	32859911
AllCCS	[M+NH4]+	168.0	32859911
AllCCS	[M+Na]+	169.0	32859911
AllCCS	[M-H]-	164.1	32859911
AllCCS	[M+Na-2H]-	163.3	32859911
AllCCS	[M+HCOO]-	162.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3'-Hydroxygenistein	OC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C(O)=C1	4464.2	Standard polar	33892256
3'-Hydroxygenistein	OC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C(O)=C1	2974.2	Standard non polar	33892256
3'-Hydroxygenistein	OC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C(O)=C1	3085.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3'-Hydroxygenistein,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C(O)=C3)=COC2=C1	3243.6	Semi standard non polar	33892256
3'-Hydroxygenistein,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C(O)=C1)=CO2	3192.3	Semi standard non polar	33892256
3'-Hydroxygenistein,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O	3244.4	Semi standard non polar	33892256
3'-Hydroxygenistein,1TMS,isomer #4	C[Si](C)(C)OC1=CC(C2=COC3=CC(O)=CC(O)=C3C2=O)=CC=C1O	3237.1	Semi standard non polar	33892256
3'-Hydroxygenistein,2TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O)C(O)=C3)=COC2=C1	3099.1	Semi standard non polar	33892256
3'-Hydroxygenistein,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)=COC2=C1	3152.0	Semi standard non polar	33892256
3'-Hydroxygenistein,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)=COC2=C1	3115.0	Semi standard non polar	33892256
3'-Hydroxygenistein,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O	3084.5	Semi standard non polar	33892256
3'-Hydroxygenistein,2TMS,isomer #5	C[Si](C)(C)OC1=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)=CC=C1O	3057.9	Semi standard non polar	33892256
3'-Hydroxygenistein,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C	3041.0	Semi standard non polar	33892256
3'-Hydroxygenistein,3TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)=COC2=C1	3050.7	Semi standard non polar	33892256
3'-Hydroxygenistein,3TMS,isomer #2	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)=COC2=C1	3017.4	Semi standard non polar	33892256
3'-Hydroxygenistein,3TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)=COC2=C1	2995.6	Semi standard non polar	33892256
3'-Hydroxygenistein,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C	2954.9	Semi standard non polar	33892256
3'-Hydroxygenistein,4TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)=COC2=C1	3002.7	Semi standard non polar	33892256
3'-Hydroxygenistein,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C(O)=C3)=COC2=C1	3515.2	Semi standard non polar	33892256
3'-Hydroxygenistein,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C(O)=C1)=CO2	3458.6	Semi standard non polar	33892256
3'-Hydroxygenistein,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O	3521.7	Semi standard non polar	33892256
3'-Hydroxygenistein,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(C2=COC3=CC(O)=CC(O)=C3C2=O)=CC=C1O	3496.9	Semi standard non polar	33892256
3'-Hydroxygenistein,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O)C(O)=C3)=COC2=C1	3693.7	Semi standard non polar	33892256
3'-Hydroxygenistein,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)=COC2=C1	3728.9	Semi standard non polar	33892256
3'-Hydroxygenistein,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)=COC2=C1	3691.7	Semi standard non polar	33892256
3'-Hydroxygenistein,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O	3685.7	Semi standard non polar	33892256
3'-Hydroxygenistein,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC=C1O	3651.3	Semi standard non polar	33892256
3'-Hydroxygenistein,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3679.8	Semi standard non polar	33892256
3'-Hydroxygenistein,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)=COC2=C1	3827.5	Semi standard non polar	33892256
3'-Hydroxygenistein,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)=COC2=C1	3801.1	Semi standard non polar	33892256
3'-Hydroxygenistein,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)=COC2=C1	3785.7	Semi standard non polar	33892256
3'-Hydroxygenistein,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3736.7	Semi standard non polar	33892256
3'-Hydroxygenistein,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)=COC2=C1	3920.1	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 - 3'-Hydroxygenistein GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0390000000-360652882f44b694b8a2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3'-Hydroxygenistein GC-MS (4 TMS) - 70eV, Positive	splash10-0zmj-1050090000-909e736154fd67b61eee	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3'-Hydroxygenistein 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 - 3'-Hydroxygenistein 10V, Positive-QTOF	splash10-000i-0090000000-d8988c733e9e4df4bfba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 20V, Positive-QTOF	splash10-052r-0190000000-347483b589c525c2fcdd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 40V, Positive-QTOF	splash10-0561-8970000000-3d0b46ec82c93f615c73	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 10V, Negative-QTOF	splash10-000i-0090000000-9f7fc9fd5ad08a4e2ad9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 20V, Negative-QTOF	splash10-000i-0290000000-459546584a2daa02d9ac	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 40V, Negative-QTOF	splash10-0ar0-0890000000-05cce6d7cfefddb81454	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 10V, Positive-QTOF	splash10-000i-0090000000-ad6070afb384abda8f3b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 20V, Positive-QTOF	splash10-000i-0090000000-f1461cca4e9ac5b2e7f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 40V, Positive-QTOF	splash10-004j-0490000000-3ed95cff32fb341dc501	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 10V, Negative-QTOF	splash10-000i-0090000000-3713e1ac18e8a67ad454	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 20V, Negative-QTOF	splash10-000i-0090000000-ed604628cd07f974a5b6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 40V, Negative-QTOF	splash10-0udi-1090000000-c3721d2c48ba328d8a20	2021-09-22	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 903	15506819	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Orobol

METLIN ID

Not Available

PubChem Compound

5281801

PDB ID

Not Available

ChEBI ID

69437

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. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

3'-Hydroxygenistein → 5,7-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one	details

Enzyme Details

2. 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

3'-Hydroxygenistein → 6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
3'-Hydroxygenistein → 6-{[3-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

3. 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

3'-Hydroxygenistein → [5-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxyphenyl]oxidanesulfonic acid	details

Showing metabocard for 3'-Hydroxygenistein (HMDB0041658)

MOL for HMDB0041658 (3'-Hydroxygenistein)

3D MOL for HMDB0041658 (3'-Hydroxygenistein)

3D SDF for HMDB0041658 (3'-Hydroxygenistein)

3D-SDF for HMDB0041658 (3'-Hydroxygenistein)

PDB for HMDB0041658 (3'-Hydroxygenistein)

3D PDB for HMDB0041658 (3'-Hydroxygenistein)

SMILES for HMDB0041658 (3'-Hydroxygenistein)

INCHI for HMDB0041658 (3'-Hydroxygenistein)

Structure for HMDB0041658 (3'-Hydroxygenistein)

3D Structure for HMDB0041658 (3'-Hydroxygenistein)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

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