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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-04-12 17:05:12 UTC

Update Date

2021-09-14 15:47:52 UTC

HMDB ID

HMDB0005897

Secondary Accession Numbers

HMDB05897

Metabolite Identification

Common Name

Dihydrogenistein

Description

Dihydrogenistein is a metabolite of the soy isoflavone genistin (the glycoside conjugate of genistein) by intestinal bacteria. Isoflavones are one of the three major classes of phytoestrogens; phytoestrogens are a diverse group of plant-derived compounds that structurally and functionally mimic mammalian estrogen. The isoflavone genistin is one of the most prevalent in soy foods. They are biologically inactive; once ingested, they are cleaved by glucosidases to "aglycones", genistein. Epidemiological studies have associated high soy intake with a lowered risk for certain hormone-dependent disease. Many studies reveal that the incidence of prostate cancer and breast cancer is much lower in Asian people in comparison to people from the West and, and the prevailing contribution to this difference has been attributed to the diet. Soy foods and soy-derived products which contain abundant isoflavones are consumed in large quantities by Asian people. In vitro, isoflavone metabolites have dual functions: they can act as an estrogenic agonist or antagonist depending on the estrogen concentration. (PMID: 17499260 , 16965913 ). Dihydrogenistein is a biomarker for the consumption of soy beans and other soy products.

Structure

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

HMDB0005897
     RDKit          3D
Dihydrogenistein
 32 34  0  0  0  0  0  0  0  0999 V2000
   -0.9203   -2.4846    0.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7988   -1.3240    0.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7980   -0.3481    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5157   -0.4064   -0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3046   -1.4436   -1.8589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663    0.5821   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816    1.6263   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6195    2.6312   -0.7079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483    1.6703    0.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155    0.7091    1.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2676    0.7112    2.2082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0464    0.2357    2.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408   -0.9825    1.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5722   -0.6898    0.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6693   -1.4979    0.8808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8570   -1.2652    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9285   -0.2039   -0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1061    0.0648   -1.4095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394    0.6193   -0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6856    0.3569   -0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7219   -2.2094   -1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048    0.5030   -2.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1347    2.5617   -1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1331    2.4987    1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2130   -0.0400    3.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7299    1.0858    2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -1.8792    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6516   -2.3303    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7339   -1.8862    0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7539    0.6895   -0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9017    1.4597   -1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067    0.9859   -0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 13  2  1  0
 20 14  1  0
 10  3  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END


  Mrv0541 02231220312D          

 20 22  0  0  0  0            999 V2000
   18.0816   -3.4558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0816   -5.9308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5240   -5.9593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9940   -3.4358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5092   -6.3433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3671   -4.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3671   -3.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0816   -5.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6527   -5.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7960   -4.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7960   -3.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5335   -5.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6527   -5.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9382   -4.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5335   -3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2810   -4.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2810   -3.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9382   -6.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2237   -5.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2237   -5.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 11  1  0  0  0  0
  2  8  2  0  0  0  0
  3 12  1  0  0  0  0
  4 17  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 15  2  0  0  0  0
 12 16  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  2  0  0  0  0
 15 17  1  0  0  0  0
 16 17  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005897

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-6,11,16-18H,7H2

> <INCHI_KEY>
UQGVUYNHDKMLSE-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.2528

> <EXACT_MASS>
272.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.587664373167307

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
2.7276581139999996

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.47348114517299

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8952448344775

> <JCHEM_PKA_STRONGEST_BASIC>
-3.864851377500867

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.67650000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrogenistein

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005897
     RDKit          3D
Dihydrogenistein
 32 34  0  0  0  0  0  0  0  0999 V2000
   -0.9203   -2.4846    0.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7988   -1.3240    0.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7980   -0.3481    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5157   -0.4064   -0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3046   -1.4436   -1.8589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663    0.5821   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816    1.6263   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6195    2.6312   -0.7079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483    1.6703    0.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155    0.7091    1.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2676    0.7112    2.2082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0464    0.2357    2.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408   -0.9825    1.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5722   -0.6898    0.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6693   -1.4979    0.8808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8570   -1.2652    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9285   -0.2039   -0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1061    0.0648   -1.4095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394    0.6193   -0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6856    0.3569   -0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7219   -2.2094   -1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048    0.5030   -2.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1347    2.5617   -1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1331    2.4987    1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2130   -0.0400    3.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7299    1.0858    2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -1.8792    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6516   -2.3303    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7339   -1.8862    0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7539    0.6895   -0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9017    1.4597   -1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067    0.9859   -0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 13  2  1  0
 20 14  1  0
 10  3  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      33.752  -6.451   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      33.752 -11.071   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      36.445 -11.124   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      39.189  -6.413   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      27.084 -11.841   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      32.419  -8.761   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.419  -7.221   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.752  -9.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.085  -9.531   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.086  -8.761   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      35.086  -7.221   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.463  -9.584   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.085 -11.071   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.751  -8.761   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      36.463  -6.397   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.858  -8.793   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.858  -7.189   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.751 -11.841   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.418  -9.531   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.418 -11.071   0.000  0.00  0.00           C+0
CONECT    1    7   11                                                       
CONECT    2    8                                                            
CONECT    3   12                                                            
CONECT    4   17                                                            
CONECT    5   20                                                            
CONECT    6    7    8    9                                                  
CONECT    7    1    6                                                       
CONECT    8    2    6   10                                                  
CONECT    9    6   13   14                                                  
CONECT   10    8   11   12                                                  
CONECT   11    1   10   15                                                  
CONECT   12    3   10   16                                                  
CONECT   13    9   18                                                       
CONECT   14    9   19                                                       
CONECT   15   11   17                                                       
CONECT   16   12   17                                                       
CONECT   17    4   15   16                                                  
CONECT   18   13   20                                                       
CONECT   19   14   20                                                       
CONECT   20    5   18   19                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0005897
HETATM    1  O1  UNL     1      -0.920  -2.485   0.167  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.799  -1.324   0.587  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.798  -0.348   0.179  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.516  -0.406  -0.985  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.305  -1.444  -1.859  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.466   0.582  -1.302  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.682   1.626  -0.430  1.00  0.00           C  
HETATM    8  O3  UNL     1      -4.619   2.631  -0.708  1.00  0.00           O  
HETATM    9  C6  UNL     1      -2.948   1.670   0.741  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.015   0.709   1.062  1.00  0.00           C  
HETATM   11  O4  UNL     1      -1.268   0.711   2.208  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.046   0.236   2.321  1.00  0.00           C  
HETATM   13  C9  UNL     1       0.341  -0.982   1.475  1.00  0.00           C  
HETATM   14  C10 UNL     1       1.572  -0.690   0.712  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.669  -1.498   0.881  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.857  -1.265   0.184  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.929  -0.204  -0.689  1.00  0.00           C  
HETATM   18  O5  UNL     1       5.106   0.065  -1.409  1.00  0.00           O  
HETATM   19  C14 UNL     1       2.839   0.619  -0.873  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.686   0.357  -0.168  1.00  0.00           C  
HETATM   21  H1  UNL     1      -1.722  -2.209  -1.868  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.005   0.503  -2.215  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.135   2.562  -1.575  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.133   2.499   1.410  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.213  -0.040   3.393  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.730   1.086   2.100  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.495  -1.879   2.120  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.652  -2.330   1.549  1.00  0.00           H  
HETATM   29  H9  UNL     1       4.734  -1.886   0.300  1.00  0.00           H  
HETATM   30  H10 UNL     1       5.754   0.690  -0.940  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.902   1.460  -1.567  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.807   0.986  -0.289  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   10
CONECT    4    5    6
CONECT    5   21
CONECT    6    7    7   22
CONECT    7    8    9
CONECT    8   23
CONECT    9   10   10   24
CONECT   10   11
CONECT   11   12
CONECT   12   13   25   26
CONECT   13   14   27
CONECT   14   15   15   20
CONECT   15   16   28
CONECT   16   17   17   29
CONECT   17   18   19
CONECT   18   30
CONECT   19   20   20   31
CONECT   20   32
END

HMDB0005897
     RDKit          3D
Dihydrogenistein
 32 34  0  0  0  0  0  0  0  0999 V2000
   -0.9203   -2.4846    0.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7988   -1.3240    0.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7980   -0.3481    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5157   -0.4064   -0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3046   -1.4436   -1.8589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663    0.5821   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816    1.6263   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6195    2.6312   -0.7079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483    1.6703    0.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155    0.7091    1.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2676    0.7112    2.2082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0464    0.2357    2.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408   -0.9825    1.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5722   -0.6898    0.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6693   -1.4979    0.8808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8570   -1.2652    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9285   -0.2039   -0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1061    0.0648   -1.4095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394    0.6193   -0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6856    0.3569   -0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7219   -2.2094   -1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048    0.5030   -2.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1347    2.5617   -1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1331    2.4987    1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2130   -0.0400    3.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7299    1.0858    2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -1.8792    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6516   -2.3303    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7339   -1.8862    0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7539    0.6895   -0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9017    1.4597   -1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067    0.9859   -0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 13  2  1  0
 20 14  1  0
 10  3  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3-Dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
4',5,7-Trihydroxyisoflavan-4-one	ChEBI
4',5,7-Trihydroxyisoflavanone	ChEBI
4',5,7-Trihydroxy-isoflavanone	HMDB

Chemical Formula

C₁₅H₁₂O₅

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

IUPAC Name

5,7-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

dihydrogenistein

CAS Registry Number

21554-71-2

SMILES

OC1=CC=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-6,11,16-18H,7H2

InChI Key

UQGVUYNHDKMLSE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanones

Alternative Parents

Substituents

Isoflavanone
Isoflavanol
Hydroxyisoflavonoid
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavanone (CHEBI:34707 )

Ontology

Physiological effect

Health effect

Ileostomy (HMDB: HMDB0005897)

Disposition

Biological location

Biofluid or Excreta

Non-excretory biofluid

Blood (HMDB: HMDB0005897)

Blood (HMDB: HMDB0005897)

Excreta

Urine (PMID: 17413104)

Cellular substructure

Membrane (HMDB: HMDB0005897)

Membrane (HMDB: HMDB0005897)
Cell membrane (HMDB: HMDB0005897)

Source

Endogenous

Endogenous (HMDB: HMDB0005897)

Plant

Plant (HMDB: HMDB0005897)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Fruits Consumption (MarkerDB: MDB00000475)
Vegetables Consumption (MarkerDB: MDB00000475)
Soy Foods Consumption (MarkerDB: MDB00000475)
Fats Consumption (MarkerDB: MDB00000475)

Physical Properties

State

Solid

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	0.23 g/L	ALOGPS
logP	2.45	ALOGPS
logP	2.73	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.9	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.68 m³·mol⁻¹	ChemAxon
Polarizability	26.59 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
DarkChem	[M+H]+	163.168	31661259
DarkChem	[M-H]-	161.724	31661259
DeepCCS	[M+H]+	160.452	30932474
DeepCCS	[M-H]-	158.094	30932474
DeepCCS	[M-2H]-	190.98	30932474
DeepCCS	[M+Na]+	166.545	30932474
AllCCS	[M+H]+	162.5	32859911
AllCCS	[M+H-H2O]+	158.7	32859911
AllCCS	[M+NH4]+	166.1	32859911
AllCCS	[M+Na]+	167.1	32859911
AllCCS	[M-H]-	163.9	32859911
AllCCS	[M+Na-2H]-	163.3	32859911
AllCCS	[M+HCOO]-	162.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrogenistein	OC1=CC=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O	3807.1	Standard polar	33892256
Dihydrogenistein	OC1=CC=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O	2858.1	Standard non polar	33892256
Dihydrogenistein	OC1=CC=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O	2887.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrogenistein,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC(O)=C3C2=O)C=C1	2823.6	Semi standard non polar	33892256
Dihydrogenistein,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C=C3)COC2=C1	2785.3	Semi standard non polar	33892256
Dihydrogenistein,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C=C1)CO2	2813.6	Semi standard non polar	33892256
Dihydrogenistein,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1	2779.1	Semi standard non polar	33892256
Dihydrogenistein,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1	2814.2	Semi standard non polar	33892256
Dihydrogenistein,2TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C(=O)C(C3=CC=C(O)C=C3)CO2)C(O[Si](C)(C)C)=C1	2822.5	Semi standard non polar	33892256
Dihydrogenistein,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1	2783.0	Semi standard non polar	33892256
Dihydrogenistein,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC(O)=C3C2=O)C=C1	3090.0	Semi standard non polar	33892256
Dihydrogenistein,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C=C3)COC2=C1	3060.1	Semi standard non polar	33892256
Dihydrogenistein,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C=C1)CO2	3071.2	Semi standard non polar	33892256
Dihydrogenistein,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1	3293.4	Semi standard non polar	33892256
Dihydrogenistein,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1	3312.2	Semi standard non polar	33892256
Dihydrogenistein,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)C(C3=CC=C(O)C=C3)CO2)C(O[Si](C)(C)C(C)(C)C)=C1	3312.4	Semi standard non polar	33892256
Dihydrogenistein,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1	3468.5	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 - Dihydrogenistein GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-2790000000-26db6a2e908263b72058	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrogenistein GC-MS (3 TMS) - 70eV, Positive	splash10-02mi-3941800000-9c483503cacf880146ba	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrogenistein 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 - Dihydrogenistein 10V, Positive-QTOF	splash10-00di-0290000000-4644374ce6fee99f6a89	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrogenistein 20V, Positive-QTOF	splash10-0pi0-0970000000-1c5b97d1c0ef243d1eff	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrogenistein 40V, Positive-QTOF	splash10-1009-6910000000-ed3a33c853a4d6d2415b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrogenistein 10V, Negative-QTOF	splash10-00di-0090000000-7a34d9e990680fc5c671	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrogenistein 20V, Negative-QTOF	splash10-00di-0290000000-811724fce8e1beb6ab95	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrogenistein 40V, Negative-QTOF	splash10-05mo-5920000000-87f0fb1a3e444af53d71	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrogenistein 10V, Positive-QTOF	splash10-00di-0090000000-031a5312b116bdf1aa4a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrogenistein 20V, Positive-QTOF	splash10-0uk9-0960000000-6d1406b5d9d548a528a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrogenistein 40V, Positive-QTOF	splash10-0py3-9830000000-dc4e3eb841ad10a12b2e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrogenistein 10V, Negative-QTOF	splash10-00di-0090000000-d6b6f6391b4e9f4522f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrogenistein 20V, Negative-QTOF	splash10-00di-0390000000-9cd64fafd3b06b9faac0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrogenistein 40V, Negative-QTOF	splash10-014u-6980000000-881132da1830614a043e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 864	15506819	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 864	15113171	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 864	10527518	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 864	14698210	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 864	10509897	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 864	7662591	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 864	17499260	details
Urine	Detected and Quantified	0.0215 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	22493748	details
Urine	Detected and Quantified	0.0904 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	20385037	details
Urine	Detected and Quantified	0.124 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	20385037	details
Urine	Detected and Quantified	21.7 +/- 6.0 (2.8 - 34.5) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17413104	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.48 +/-0.27 (0.3 - 1.5) umol/mmol creatinine	Adult (>18 years old)	Both	Soy consumption (ileostomies)	17413104	details

Associated Disorders and Diseases

Disease References

Ileostomy
Walsh KR, Haak SJ, Bohn T, Tian Q, Schwartz SJ, Failla ML: Isoflavonoid glucosides are deconjugated and absorbed in the small intestine of human subjects with ileostomies. Am J Clin Nutr. 2007 Apr;85(4):1050-6. [PubMed:17413104 ]

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

Not Available

METLIN ID

Not Available

PubChem Compound

9838356

PDB ID

Not Available

ChEBI ID

34707

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000475

Good Scents ID

Not Available

References

Synthesis Reference

Inoue, Naoto. Studies on synthetic isoflavanones. III. Alkaline degradation of synthetic isoflavones and isoflavanones. Sci. Repts. Tohoku Univ., First Ser. (1961), 45(No. 1), 73-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Chen L, Zhao X, Fang L, Games DE: Quantitative determination of acetyl glucoside isoflavones and their metabolites in human urine using combined liquid chromatography-mass spectrometry. J Chromatogr A. 2007 Jun 22;1154(1-2):103-10. Epub 2007 Mar 15. [PubMed:17499260 ]
Hwang CS, Kwak HS, Lim HJ, Lee SH, Kang YS, Choe TB, Hur HG, Han KO: Isoflavone metabolites and their in vitro dual functions: they can act as an estrogenic agonist or antagonist depending on the estrogen concentration. J Steroid Biochem Mol Biol. 2006 Nov;101(4-5):246-53. Epub 2006 Sep 11. [PubMed:16965913 ]

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

Dihydrogenistein → 3,4,5-trihydroxy-6-{[7-hydroxy-3-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic acid	details
Dihydrogenistein → 3,4,5-trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid	details
Dihydrogenistein → 6-[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]-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

Dihydrogenistein → [4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenyl]oxidanesulfonic acid	details

Showing metabocard for Dihydrogenistein (HMDB0005897)

MOL for HMDB0005897 (Dihydrogenistein)

3D MOL for HMDB0005897 (Dihydrogenistein)

3D SDF for HMDB0005897 (Dihydrogenistein)

3D-SDF for HMDB0005897 (Dihydrogenistein)

PDB for HMDB0005897 (Dihydrogenistein)

3D PDB for HMDB0005897 (Dihydrogenistein)

SMILES for HMDB0005897 (Dihydrogenistein)

INCHI for HMDB0005897 (Dihydrogenistein)

Structure for HMDB0005897 (Dihydrogenistein)

3D Structure for HMDB0005897 (Dihydrogenistein)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions