Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (3) Show 12 proteins XML

enzymes (9)transporters (3) Show 12 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:42 UTC

Update Date

2022-03-07 02:49:18 UTC

HMDB ID

HMDB0003217

Secondary Accession Numbers

HMDB03217

Metabolite Identification

Common Name

Genistein

Description

Genistein is one of several known isoflavones. Isoflavones compounds, such as genistein and daidzein, are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Genistein is a natural bioactive compound derived from legumes and has drawn because of its potentially beneficial effects on some human degenerative diseases. It has a weak estrogenic effect and is a well-known non-specific tyrosine kinase inhibitor at pharmacological doses. Epidemiological studies show that genistein intake is inversely associated with the risk of cardiovascular diseases. Data suggests a protective role of genistein in cardiovascular events. However, the mechanisms of the genistein action on vascular protective effects are unclear. Past extensive studies exploring its hypolipidemic effect resulted in contradictory data. Genistein also is a relatively poor antioxidant. However, genistein protects against pro-inflammatory factor-induced vascular endothelial barrier dysfunction and inhibits leukocyte-endothelium interaction, thereby modulating vascular inflammation, a major event in the pathogenesis of atherosclerosis. Genistein exerts a non-genomic action by targeting on important signaling molecules in vascular endothelial cells (ECs). Genistein rapidly activates endothelial nitric oxide synthase and production of nitric oxide in ECs. This genistein effect is novel since it is independent of its known effects, but mediated by the cyclic adenosine monophosphate/protein kinase A (cAMP/PKA) cascade. Genistein directly stimulates the plasma membrane-associated adenylate cyclases, leading to activation of the cAMP signaling pathway. In addition, genistein activates peroxisome proliferator-activated receptors, ligand-activated nuclear receptors important to normal vascular function. Furthermore, genistein reduces reactive oxygen species (ROS) by attenuating the expression of ROS-producing enzymes. These findings reveal the roles for genistein in the regulation of vascular function and provide a basis for further investigating its therapeutic potential for inflammatory-related vascular disease. (PMID:17979711 ). Genistein 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

HMDB0003217
     RDKit          3D
Genistein
 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.0402   -1.7344    0.0988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -0.5720    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4118    0.4719    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683    0.2154    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4155   -0.7219    0.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7751   -0.9613    0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443   -0.2898    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0152   -0.5470    0.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0963    0.6475   -0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7360    0.8881   -0.7655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0793    1.7546    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599    1.9821    0.0527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615    1.0396    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6135    1.3311    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5309    0.3239    0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8789    0.6524    0.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1725   -0.9936    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -1.2864    0.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4650   -2.6002    0.1153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8355   -0.2968    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7623   -1.2660    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2385   -1.7008    1.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6498   -0.0267    0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7848    1.1720   -1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059    1.6283   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6548    2.5717    0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8951    2.3796    0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4368    0.7773   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902   -1.8049    0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189   -3.0337    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 10  4  1  0
 20 13  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END

Genistein
  Mrv1652305201900042D          

 20 22  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
    3.0723   -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
    3.0723   -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
    0.9289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2144   -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
   -1.9290    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
    0.2144   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 18  1  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
M  END
> <DATABASE_ID>
HMDB0003217

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H

> <INCHI_KEY>
TZBJGXHYKVUXJN-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.24

> <EXACT_MASS>
270.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.58861830751393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
3.076872389666666

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.088397479737148

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.5462698153602235

> <JCHEM_PKA_STRONGEST_BASIC>
-5.345613136233476

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.68290000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
genistein

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003217
     RDKit          3D
Genistein
 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.0402   -1.7344    0.0988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -0.5720    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4118    0.4719    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683    0.2154    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4155   -0.7219    0.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7751   -0.9613    0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443   -0.2898    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0152   -0.5470    0.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0963    0.6475   -0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7360    0.8881   -0.7655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0793    1.7546    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599    1.9821    0.0527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615    1.0396    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6135    1.3311    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5309    0.3239    0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8789    0.6524    0.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1725   -0.9936    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -1.2864    0.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4650   -2.6002    0.1153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8355   -0.2968    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7623   -1.2660    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2385   -1.7008    1.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6498   -0.0267    0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7848    1.1720   -1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059    1.6283   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6548    2.5717    0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8951    2.3796    0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4368    0.7773   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902   -1.8049    0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189   -3.0337    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 10  4  1  0
 20 13  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Genistein                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         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
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0003217
HETATM    1  O1  UNL     1      -0.040  -1.734   0.099  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.488  -0.572   0.084  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.412   0.472   0.069  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.868   0.215   0.069  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.415  -0.722   0.920  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.775  -0.961   0.920  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.644  -0.290   0.086  1.00  0.00           C  
HETATM    8  O2  UNL     1       6.015  -0.547   0.103  1.00  0.00           O  
HETATM    9  C7  UNL     1       4.096   0.647  -0.764  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.736   0.888  -0.766  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.079   1.755   0.053  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.360   1.982   0.053  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.262   1.040   0.067  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.614   1.331   0.066  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.531   0.324   0.081  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.879   0.652   0.080  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.172  -0.994   0.098  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.792  -1.286   0.099  1.00  0.00           C  
HETATM   19  O5  UNL     1      -2.465  -2.600   0.115  1.00  0.00           O  
HETATM   20  C15 UNL     1      -1.835  -0.297   0.084  1.00  0.00           C  
HETATM   21  H1  UNL     1       1.762  -1.266   1.586  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.239  -1.701   1.586  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.650  -0.027   0.721  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.785   1.172  -1.417  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.306   1.628  -1.438  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.655   2.572   0.041  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.895   2.380   0.053  1.00  0.00           H  
HETATM   28  H8  UNL     1      -6.437   0.777  -0.734  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.890  -1.805   0.110  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.619  -3.034   0.119  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4   11   11
CONECT    4    5    5   10
CONECT    5    6   21
CONECT    6    7    7   22
CONECT    7    8    9
CONECT    8   23
CONECT    9   10   10   24
CONECT   10   25
CONECT   11   12   26
CONECT   12   13
CONECT   13   14   14   20
CONECT   14   15   27
CONECT   15   16   17   17
CONECT   16   28
CONECT   17   18   29
CONECT   18   19   20   20
CONECT   19   30
END

HMDB0003217
     RDKit          3D
Genistein
 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.0402   -1.7344    0.0988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884   -0.5720    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4118    0.4719    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683    0.2154    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4155   -0.7219    0.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7751   -0.9613    0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443   -0.2898    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0152   -0.5470    0.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0963    0.6475   -0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7360    0.8881   -0.7655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0793    1.7546    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599    1.9821    0.0527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615    1.0396    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6135    1.3311    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5309    0.3239    0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8789    0.6524    0.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1725   -0.9936    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -1.2864    0.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4650   -2.6002    0.1153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8355   -0.2968    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7623   -1.2660    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2385   -1.7008    1.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6498   -0.0267    0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7848    1.1720   -1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059    1.6283   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6548    2.5717    0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8951    2.3796    0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4368    0.7773   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902   -1.8049    0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189   -3.0337    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 10  4  1  0
 20 13  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4',5,7-Trihydroxyisoflavone	ChEBI
5,7,4'-Trihydroxyisoflavone	ChEBI
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
Prunetol	ChEBI
Sophoricol	ChEBI
4',5, 7-Trihydroxyisoflavone	HMDB
4',5,7-Trihydroxy-isoflavone	HMDB
4,5,7-Trihydroxy iso-flavone	HMDB
Genistein 85% HPLC	HMDB
Genisteol	HMDB
Genisterin	HMDB
Genestein	HMDB

Chemical Formula

C₁₅H₁₀O₅

Average Molecular Weight

270.24

Monoisotopic Molecular Weight

270.052823422

IUPAC Name

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

Traditional Name

genistein

CAS Registry Number

446-72-0

SMILES

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

InChI Identifier

InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:28088 )
isoflavones (C06563 )
Isoflavonoids (C06563 )
Isoflavonoids (LMPK12050218 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Gastrointestinal disorder

Lower gastrointestinal disorder

Ileostomy (HMDB: HMDB0003217)

Organoleptic effect

Taste

Bitter

Adipose tissue (HMDB: HMDB0003217)
Adipose tissue (HMDB: HMDB0003217)

Epithelium

Epidermis (HMDB: HMDB0003217)

Muscle tissue

Skeletal muscle (HMDB: HMDB0003217)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17449595)

Cellular substructure

Membrane (HMDB: HMDB0003217)
Cell membrane (HMDB: HMDB0003217)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0003217)

Hematocyte

Platelet (HMDB: HMDB0003217)

Tissue substructure

Muscle (HMDB: HMDB0003217)

Organ

Gland

Adrenal Gland (HMDB: HMDB0003217)
Adrenal Gland (HMDB: HMDB0003217)

Excreta

Biofluid or Excreta

Urine (PMID: 17413104)
Feces (PMID: 27275383)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003217)

Source

Exogenous

Exogenous (HMDB: HMDB0003217)

Food

Food (HMDB: HMDB0003217)
Legumes (HMDB: HMDB0003217)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Leavened bread

Wheat bread (FooDB: FOOD00808)
Multigrain bread (FooDB: FOOD00814)

Cereal

Cereal product

Bread products

Other bread product (FooDB: FOOD00805)

Flat bread

Crisp bread (FooDB: FOOD00640)

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)
Soy (HMDB: HMDB0003217)

Soy product

Animal origin

Bovine

Cattle (Beef, Veal) (FooDB: FOOD00495)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Other beverage

Vegetable juice (FooDB: FOOD00822)

Nutritional beverage

Nutritional drink (FooDB: FOOD00754)

Dish

Ground meat

Sausage (FooDB: FOOD00652)

Other dish

Tex-mex cuisine

Chili (FooDB: FOOD00707)

Levantine cuisine

Hummus (FooDB: FOOD00845)

Berber cuisine

Couscous (FooDB: FOOD00740)

Fat and oil

Vegetable fat

Margarine-like spread (FooDB: FOOD00844)

Aquatic origin

Fish

Fish product

Other fish product (FooDB: FOOD00665)

Seaweed

Mollusk

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Coffee and coffee product

Pastry (FooDB: FOOD00641)
Cake (FooDB: FOOD00636)

Milk and milk product

Fermented milk product

Yogurt (FooDB: FOOD00620)

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Other milk product

Salted butter (FooDB: FOOD00939)

Egg

Eggs (FooDB: FOOD00619)

Baking good

Dressing

Salad dressing (FooDB: FOOD00645)

Sauce

Sauce (FooDB: FOOD00646)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Synthetic

Personal care products

Personal care products (HMDB: HMDB0003217)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0003217)

Process

Not Available

Role

Industrial application

Personal care product

Personal care product (HMDB: HMDB0003217)

Pharmaceutical industry

Antineoplastic agent

Biomarker

Fruits Consumption (MarkerDB: MDB00000414)
Vegetables Consumption (MarkerDB: MDB00000414)
Soy Foods Consumption (MarkerDB: MDB00000414)
Fats Consumption (MarkerDB: MDB00000414)
Dietary Fibre Consumption (MarkerDB: MDB00000414)
Genistein Exposure (MarkerDB: MDB00000414)

Antineoplastic agent (HMDB: HMDB0003217)
Antiviral agent (HMDB: HMDB0003217)
Abortifacient (HMDB: HMDB0003217)

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Coloring agent

Fluorescent agent

Immunological adjuvant (HMDB: HMDB0003217)

Agriculture

Pesticide

Fungicide (HMDB: HMDB0003217)

Pesticide (HMDB: HMDB0003217)

Biological role

Plant metabolite (HMDB: HMDB0003217)
Phytoestrogen (HMDB: HMDB0003217)
Antiangiogenic (HMDB: HMDB0003217)
Antiangiogenic (HMDB: HMDB0003217)
Calcium antagonist (HMDB: HMDB0003217)
VEGF inhibitor (HMDB: HMDB0003217)
Anti aggregant (HMDB: HMDB0003217)
Anti atherosclerotic (HMDB: HMDB0003217)
Anti cancer (HMDB: HMDB0003217)
Anti carcinomic (HMDB: HMDB0003217)
Anti climacteric (HMDB: HMDB0003217)
Anti endoccytotic (HMDB: HMDB0003217)
Anti-estrogenic (HMDB: HMDB0003217)
Anti fertility (HMDB: HMDB0003217)
Anti hemolytic (HMDB: HMDB0003217)
Anti implantation (HMDB: HMDB0003217)
Anti-inflammatory (HMDB: HMDB0003217)
Anti ischemic (HMDB: HMDB0003217)
Anti leukemic (HMDB: HMDB0003217)
Anti leukotriene (HMDB: HMDB0003217)
Anti lymphomic (HMDB: HMDB0003217)
Anti melanomic (HMDB: HMDB0003217)
Anti microbial (HMDB: HMDB0003217)
Anti mitogenic (HMDB: HMDB0003217)
Anti mutagenic (HMDB: HMDB0003217)
Anti neuroblastomic (HMDB: HMDB0003217)
Anti osteoporotic (HMDB: HMDB0003217)
Anti proliferative (HMDB: HMDB0003217)
Anti prostat adenomic (HMDB: HMDB0003217)
Anti prostatitic (HMDB: HMDB0003217)
Anti spasmodic (HMDB: HMDB0003217)
Anti ulcer (HMDB: HMDB0003217)
Cardioprotective (HMDB: HMDB0003217)
Cytotoxic (HMDB: HMDB0003217)
Estrogen agonist (HMDB: HMDB0003217)
Estrogen receptor agonist (HMDB: HMDB0003217)
Estrogenic (HMDB: HMDB0003217)
Flatulent (HMDB: HMDB0003217)
Fungistat (HMDB: HMDB0003217)
Hypocholesterolemic (HMDB: HMDB0003217)
Natriuretic (HMDB: HMDB0003217)
Phytoalexin (HMDB: HMDB0003217)
Pituitary sensitizer (HMDB: HMDB0003217)
Quinone-reductase inducer (HMDB: HMDB0003217)
Trypanosomastat (HMDB: HMDB0003217)
Utero trophic (HMDB: HMDB0003217)

Modulator

Inhibitor

Enzyme inhibitor

Tyrosine-kinase inhibitor (HMDB: HMDB0003217)
Protein-tyrosine-kinase inhibitor (HMDB: HMDB0003217)
Tyrosine-kinase inhibitor (HMDB: HMDB0003217)
Alpha-reductase inhibitor (HMDB: HMDB0003217)
DOPA-decarboxylase inhibitor (HMDB: HMDB0003217)
Histidine-kinase inhibitor (HMDB: HMDB0003217)
Lipase inhibitor (HMDB: HMDB0003217)
Monoamine-oxidase inhibitor (HMDB: HMDB0003217)
NADH-ubiquinone-oxidoreductase inhibitor (HMDB: HMDB0003217)
Ornithine-decarboxylase inhibitor (HMDB: HMDB0003217)
Peroxidase inhibitor (HMDB: HMDB0003217)

EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (HMDB: HMDB0003217)
EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0003217)
EC 1.14.14.14 (aromatase) inhibitor (HMDB: HMDB0003217)
EC 2.1.1.6 (catechol O-methyltransferase) inhibitor (HMDB: HMDB0003217)
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor (HMDB: HMDB0003217)
EC 5.99.1.2 (DNA topoisomerase) inhibitor (HMDB: HMDB0003217)
Multidrug resistance inhibitor (HMDB: HMDB0003217)
Topoisomerase-II inhibitor (HMDB: HMDB0003217)

Apoptotic (HMDB: HMDB0003217)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	301.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	164.133	30932474
[M+H]+	Baker	163.3	30932474
[M-H]-	Not Available	164.133	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001942
[M+H]+	Not Available	163.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001942

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	3.04	ALOGPS
logP	3.08	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.55	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-1	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
DeepCCS	[M+H]+	160.719	30932474
DeepCCS	[M-H]-	158.361	30932474
DeepCCS	[M-2H]-	191.247	30932474
DeepCCS	[M+Na]+	166.812	30932474
AllCCS	[M+H]+	161.0	32859911
AllCCS	[M+H-H2O]+	157.1	32859911
AllCCS	[M+NH4]+	164.6	32859911
AllCCS	[M+Na]+	165.6	32859911
AllCCS	[M-H]-	161.5	32859911
AllCCS	[M+Na-2H]-	160.7	32859911
AllCCS	[M+HCOO]-	160.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Genistein	OC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O	4341.6	Standard polar	33892256
Genistein	OC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O	2842.4	Standard non polar	33892256
Genistein	OC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O	2965.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Genistein,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1	3073.6	Semi standard non polar	33892256
Genistein,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C=C3)=COC2=C1	3067.1	Semi standard non polar	33892256
Genistein,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C=C1)=CO2	3008.2	Semi standard non polar	33892256
Genistein,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1	3010.4	Semi standard non polar	33892256
Genistein,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1	2954.3	Semi standard non polar	33892256
Genistein,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3)=COC2=C1	2997.2	Semi standard non polar	33892256
Genistein,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1	2931.0	Semi standard non polar	33892256
Genistein,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1	3324.6	Semi standard non polar	33892256
Genistein,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C=C3)=COC2=C1	3329.7	Semi standard non polar	33892256
Genistein,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C=C1)=CO2	3259.9	Semi standard non polar	33892256
Genistein,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1	3552.4	Semi standard non polar	33892256
Genistein,2TBDMS,isomer #2	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=C1	3508.7	Semi standard non polar	33892256
Genistein,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3)=COC2=C1	3542.0	Semi standard non polar	33892256
Genistein,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1	3692.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Genistein GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-0321900000-1dd6fcaf99898bd949df	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Genistein GC-EI-TOF (Non-derivatized)	splash10-00di-0321900000-1dd6fcaf99898bd949df	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Genistein GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0490000000-2922d094b504ca63625f	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Genistein GC-MS (3 TMS) - 70eV, Positive	splash10-00di-3232900000-5532bb09d0ee2a1c2b07	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Genistein GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Genistein 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-APPI-QQ (API2000) , Positive-QTOF	splash10-014l-9600000000-04b546320e268d817276	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-APPI-QQ (API2000) , Positive-QTOF	splash10-00kf-5910000000-7e265d1b4640f882195a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-APPI-QQ (API2000) , Positive-QTOF	splash10-0v4m-1960000000-7843ec8ae23314f88147	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-APPI-QQ (API2000) , Positive-QTOF	splash10-00di-0290000000-52ec910b223a3688fbc0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-APPI-QQ (API2000) , Positive-QTOF	splash10-00di-0190000000-4045f471e10774927fb0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-APPI-QQ (API2000) , Positive-QTOF	splash10-00di-0090000000-b593f863241cb83cbaa8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-APPI-QQ (API2000) , Positive-QTOF	splash10-00di-0190000000-0cd8d123608bd54f7214	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive-QTOF	splash10-00di-0090000000-9ce354d07dc39313259b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-001i-0910000000-5eb75a138568fa4ac897	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0fr6-2920000000-a32f6ae97952bb96de05	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-00di-0290000000-4592d557e739a114cbfa	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-ESI-ITTOF (LCMS-IT-TOF) , Positive-QTOF	splash10-00di-0090000000-14ae481944ad1a1f7ca0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein LC-ESI-ITTOF (LCMS-IT-TOF) , Negative-QTOF	splash10-014i-0090030000-a3400b0a77da6983528f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein ESI-TOF , Negative-QTOF	splash10-014i-0090000000-6db4d2441911d696b121	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein ESI-TOF 20V, Negative-QTOF	splash10-014i-0090000000-6db4d2441911d696b121	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein ESI-TOF 50V, Negative-QTOF	splash10-001i-0900000000-ad50062f85b9c32e1426	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein ESI-TOF 40V, Negative-QTOF	splash10-001i-0910000000-6a694e60823635f66757	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein ESI-TOF , Negative-QTOF	splash10-014i-0090000000-720c4e1f43db9f50b589	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Genistein ESI-TOF 20V, Negative-QTOF	splash10-014i-0090000000-0e3ca66534f635efb4d8	2017-09-12	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genistein 10V, Positive-QTOF	splash10-00di-0090000000-3ca72bf3c489e8b06845	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genistein 20V, Positive-QTOF	splash10-00di-0090000000-664850196c63c1380b4e	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genistein 40V, Positive-QTOF	splash10-0udi-5790000000-f3cf7e73e69ebaba0989	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genistein 10V, Negative-QTOF	splash10-014i-0090000000-aa4506f67fa71b5e6f4e	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genistein 20V, Negative-QTOF	splash10-014i-0090000000-f1f0ad0b45f461f988db	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genistein 40V, Negative-QTOF	splash10-0gb9-3960000000-16725698ad6eee8f88dc	2017-06-28	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Adipose Tissue
Adrenal Gland
Epidermis
Fibroblasts
Intestine
Liver
Neuron
Placenta
Platelet
Prostate
Skeletal Muscle
Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0065 (0.0057 - 0.0074) uM	Adult (>18 years old)	Male	Normal	17449595	details
Blood	Detected and Quantified	0.0063 (0.0056 - 0.0071) uM	Adult (>18 years old)	Female	Normal	17449595	details
Blood	Detected and Quantified	0.025 (0.000 - 0.050) uM	Adult (>18 years old)	Both	Normal	9618027	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.181 uM	Adult (>18 years old)	Female	Normal	10778038	details
Blood	Detected and Quantified	0.278 uM	Adult (>18 years old)	Female	Normal	10778038	details
Blood	Detected and Quantified	0.0122 uM	Adult (>18 years old)	Female	Normal	12600860	details
Blood	Detected and Quantified	0.0278 uM	Adult (>18 years old)	Female	Normal	11570994	details
Blood	Detected and Quantified	0.0588 uM	Adult (>18 years old)	Female	Normal	11570994	details
Blood	Detected and Quantified	0.285 uM	Adult (>18 years old)	Female	Normal	11570994	details
Blood	Detected and Quantified	0.525 uM	Adult (>18 years old)	Female	Normal	11570994	details
Blood	Detected and Quantified	0.0169 uM	Adult (>18 years old)	Both	Normal	12396157	details
Blood	Detected and Quantified	0.246 uM	Adult (>18 years old)	Both	Normal	15005831	details
Blood	Detected and Quantified	0.475 +/- 0.510 uM	Adult (>18 years old)	Both	Normal	11584098	details
Blood	Detected and Quantified	0.0027 uM	Adult (>18 years old)	Female	Normal	20332276	details
Blood	Detected and Quantified	0.0057 uM	Adult (>18 years old)	Female	Normal	9796633	details
Blood	Detected and Quantified	0.00925 uM	Adult (>18 years old)	Female	Normal	9796633	details
Blood	Detected and Quantified	0.013 uM	Adult (>18 years old)	Female	Normal	15159299	details
Blood	Detected and Quantified	0.0183 +/- 0.0207 uM	Adult (>18 years old)	Female	Normal	15623842	details
Blood	Detected and Quantified	0.00022 +/- 0.00030 uM	Adult (>18 years old)	Both	Normal	9618027	details
Blood	Detected and Quantified	0.307 +/- 0.325 uM	Adult (>18 years old)	Female	Normal	10778038	details
Blood	Detected and Quantified	0.0338 uM	Adult (>18 years old)	Male	Normal	16205743	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.028 (0.0077-0.064) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23657156	details
Urine	Detected and Quantified	0.032 +/- 0.007 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	10822017	details
Urine	Detected and Quantified	0.11 +/- 0.017 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	10822017	details
Urine	Detected and Quantified	0.0147 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.0237 +/- 0.0300 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	11410004	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	16920843	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	8017326	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	10798213	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	10952094	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	15506819	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	15113171	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	10527518	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	14698210	details
Urine	Detected and Quantified	0.707 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	10778038	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	10509897	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	20164315	details
Urine	Detected and Quantified	0.753 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	10778038	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	17579895	details
Urine	Detected and Quantified	0.0160 +/- 0.0200 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	7662591	details
Urine	Detected and Quantified	0.0140 +/- 0.0133 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	17499260	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	7722188	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	7930998	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 396	20067656	details
Urine	Detected and Quantified	0.23 +/- 0.08 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17413104	details
Urine	Detected and Quantified	0.0127 (0.0108-0.0150) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.0228 (0.0174-0.0251) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.200 +/- 0.320 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	17353586	details
Urine	Detected and Quantified	0.193 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	18469267	details
Urine	Detected and Quantified	0.0571 +/- 0.0674 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	18791925	details
Urine	Detected and Quantified	0.105 +/- 0.199 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	18791925	details
Urine	Detected and Quantified	0.00122 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19167951	details
Urine	Detected and Quantified	0.00971 umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	17976571	details
Urine	Detected and Quantified	0.0907 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	18469267	details
Urine	Detected and Quantified	0.18 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15005831	details
Urine	Detected and Quantified	0.0367 +/- 0.0813 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.947 +/- 0.940 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	11584098	details
Urine	Detected and Quantified	0.0124 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	20332276	details
Urine	Detected and Quantified	0.0185 umol/mmol creatinine	Children (1 - 13 years old)	Female	Normal	17366830	details
Urine	Detected and Quantified	0.0292 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	15159299	details
Urine	Detected and Quantified	0.215 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	20385037	details
Urine	Detected and Quantified	0.272 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	22493748	details
Urine	Detected and Quantified	0.644 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	20385037	details
Urine	Detected and Quantified	0.0192 +/- 0.0272 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.0352 +/- 0.0560 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.0448 +/- 0.0992 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.104 +/- 0.168 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.115 +/- 0.259 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.214 +/- 0.298 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.880 +/- 0.693 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	10778038	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	0.39 +/- 0.18 umol/mmol creatinine	Adult (>18 years old)	Both	Soy consumption (ileostomies)	17413104	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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

114500 (Colorectal cancer)

External Links

DrugBank ID

DB01645

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Genistein

METLIN ID

3398

PubChem Compound

5280961

PDB ID

Not Available

ChEBI ID

28088

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000414

Good Scents ID

Not Available

References

Synthesis Reference

Baker, Wilson; Robinson, Robert. Synthetical experiments in the isoflavone group. IV. Synthesis of 2-methylirigenol. Journal of the Chemical Society (1929), Volume Date 1928, 152-61.

Material Safety Data Sheet (MSDS)

Not Available

General References

Wisniewski AB, Klein SL, Lakshmanan Y, Gearhart JP: Exposure to genistein during gestation and lactation demasculinizes the reproductive system in rats. J Urol. 2003 Apr;169(4):1582-6. [PubMed:12629420 ]
Ohno S, Nakajima Y, Inoue K, Nakazawa H, Nakajin S: Genistein administration decreases serum corticosterone and testosterone levels in rats. Life Sci. 2003 Dec 26;74(6):733-42. [PubMed:14654166 ]
Kim S, Shin HJ, Kim SY, Kim JH, Lee YS, Kim DH, Lee MO: Genistein enhances expression of genes involved in fatty acid catabolism through activation of PPARalpha. Mol Cell Endocrinol. 2004 May 31;220(1-2):51-8. [PubMed:15196699 ]
de Pascual-Teresa S, Hallund J, Talbot D, Schroot J, Williams CM, Bugel S, Cassidy A: Absorption of isoflavones in humans: effects of food matrix and processing. J Nutr Biochem. 2006 Apr;17(4):257-64. [PubMed:16109484 ]
Huang X, Chen S, Xu L, Liu Y, Deb DK, Platanias LC, Bergan RC: Genistein inhibits p38 map kinase activation, matrix metalloproteinase type 2, and cell invasion in human prostate epithelial cells. Cancer Res. 2005 Apr 15;65(8):3470-8. [PubMed:15833883 ]
Ronis MJ, Little JM, Barone GW, Chen G, Radominska-Pandya A, Badger TM: Sulfation of the isoflavones genistein and daidzein in human and rat liver and gastrointestinal tract. J Med Food. 2006 Fall;9(3):348-55. [PubMed:17004897 ]
Fotsis T, Pepper MS, Aktas E, Breit S, Rasku S, Adlercreutz H, Wahala K, Montesano R, Schweigerer L: Flavonoids, dietary-derived inhibitors of cell proliferation and in vitro angiogenesis. Cancer Res. 1997 Jul 15;57(14):2916-21. [PubMed:9230201 ]
Casagrande F, Darbon JM: p21CIP1 is dispensable for the G2 arrest caused by genistein in human melanoma cells. Exp Cell Res. 2000 Jul 10;258(1):101-8. [PubMed:10912792 ]
Li Y, Ahmed F, Ali S, Philip PA, Kucuk O, Sarkar FH: Inactivation of nuclear factor kappaB by soy isoflavone genistein contributes to increased apoptosis induced by chemotherapeutic agents in human cancer cells. Cancer Res. 2005 Aug 1;65(15):6934-42. [PubMed:16061678 ]
D'Souza N, Skonberg DI, Camire ME, Guthrie KE, Malison J, Lima L: Influence of dietary genistein levels on tissue genistein deposition and on the physical, chemical, and sensory quality of rainbow trout, Oncorhynchus mykiss. J Agric Food Chem. 2005 May 4;53(9):3631-6. [PubMed:15853412 ]
Sonee M, Sum T, Wang C, Mukherjee SK: The soy isoflavone, genistein, protects human cortical neuronal cells from oxidative stress. Neurotoxicology. 2004 Sep;25(5):885-91. [PubMed:15288519 ]
Li M, Zhang Z, Hill DL, Chen X, Wang H, Zhang R: Genistein, a dietary isoflavone, down-regulates the MDM2 oncogene at both transcriptional and posttranslational levels. Cancer Res. 2005 Sep 15;65(18):8200-8. [PubMed:16166295 ]
Si H, Liu D: Phytochemical genistein in the regulation of vascular function: new insights. Curr Med Chem. 2007;14(24):2581-9. [PubMed:17979711 ]
Crisafulli A, Altavilla D, Marini H, Bitto A, Cucinotta D, Frisina N, Corrado F, D'Anna R, Squadrito G, Adamo EB, Marini R, Romeo A, Cancellieri F, Buemi M, Squadrito F: Effects of the phytoestrogen genistein on cardiovascular risk factors in postmenopausal women. Menopause. 2005 Mar;12(2):186-92. [PubMed:15772566 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Nuclear receptor coactivator 1

General function:: Involved in transcription coactivator activity
Specific function:: Nuclear receptor coactivator that directly binds nuclear receptors and stimulates the transcriptional activities in a hormone-dependent fashion. Involved in the coactivation of different nuclear receptors, such as for steroids (PGR, GR and ER), retinoids (RXRs), thyroid hormone (TRs) and prostanoids (PPARs). Also involved in coactivation mediated by STAT3, STAT5A, STAT5B and STAT6 transcription factors. Displays histone acetyltransferase activity toward H3 and H4; the relevance of such activity remains however unclear. Plays a central role in creating multisubunit coactivator complexes that act via remodeling of chromatin, and possibly acts by participating in both chromatin remodeling and recruitment of general transcription factors. Required with NCOA2 to control energy balance between white and brown adipose tissues. Required for mediating steroid hormone response. Isoform 2 has a higher thyroid hormone-dependent transactivation activity than isoform 1 and isoform 3.
Gene Name:: NCOA1
Uniprot ID:: Q15788
Molecular weight:: 156755.44

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

2. Dehydrogenase/reductase SDR family member 4

General function:: Involved in oxidoreductase activity
Specific function:: Reduces all-trans-retinal and 9-cis retinal. Can also catalyze the oxidation of all-trans-retinol with NADP as co-factor, but with much lower efficiency. Reduces alkyl phenyl ketones and alpha-dicarbonyl compounds with aromatic rings, such as pyrimidine-4-aldehyde, 3-benzoylpyridine, 4-benzoylpyridine, menadione and 4-hexanoylpyridine. Has no activity towards aliphatic aldehydes and ketones (By similarity).
Gene Name:: DHRS4
Uniprot ID:: Q9BTZ2
Molecular weight:: 29536.885

Enzyme Details

3. Estrogen receptor beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner. Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA- binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual
Gene Name:: ESR2
Uniprot ID:: Q92731
Molecular weight:: 59215.8

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

4. 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

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

Enzyme Details

5. Protein-tyrosine kinase 2-beta

General function:: Involved in binding
Specific function:: Involved in calcium induced regulation of ion channel and activation of the map kinase signaling pathway. May represent an important signaling intermediate between neuropeptide activated receptors or neurotransmitters that increase calcium flux and the downstream signals that regulate neuronal activity. Interacts with the SH2 domain of Grb2. May phosphorylate the voltage-gated potassium channel protein Kv1.2. Its activation is highly correlated with the stimulation of c-Jun N-terminal kinase activity. Involved in osmotic stress-dependent SNCA 'Tyr-125' phosphorylation
Gene Name:: PTK2B
Uniprot ID:: Q14289
Molecular weight:: 115873.6

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

6. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Hu M, Krausz K, Chen J, Ge X, Li J, Gelboin HL, Gonzalez FJ: Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones. Drug Metab Dispos. 2003 Jul;31(7):924-31. [PubMed:12814970 ]

Enzyme Details

7. Estrogen receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:: ESR1
Uniprot ID:: P03372
Molecular weight:: 66215.4

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

8. DNA topoisomerase 2-alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:: TOP2A
Uniprot ID:: P11388
Molecular weight:: 174383.9

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

9. 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

Genistein → [4-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)phenyl]oxidanesulfonic acid	details

Transporters

Enzyme Details

1. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Pec MK, Aguirre A, Fernandez JJ, Souto ML, Dorta JF, Villar J: Dehydrothyrsiferol does not modulate multidrug resistance-associated protein 1 resistance: a functional screening system for MRP1 substrates. Int J Mol Med. 2002 Nov;10(5):605-8. [PubMed:12373300 ]
Nguyen H, Zhang S, Morris ME: Effect of flavonoids on MRP1-mediated transport in Panc-1 cells. J Pharm Sci. 2003 Feb;92(2):250-7. [PubMed:12532374 ]
Hong J, Lambert JD, Lee SH, Sinko PJ, Yang CS: Involvement of multidrug resistance-associated proteins in regulating cellular levels of (-)-epigallocatechin-3-gallate and its methyl metabolites. Biochem Biophys Res Commun. 2003 Oct 10;310(1):222-7. [PubMed:14511674 ]
Versantvoort CH, Rhodes T, Twentyman PR: Acceleration of MRP-associated efflux of rhodamine 123 by genistein and related compounds. Br J Cancer. 1996 Dec;74(12):1949-54. [PubMed:8980395 ]

Enzyme Details

2. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Castro AF, Altenberg GA: Inhibition of drug transport by genistein in multidrug-resistant cells expressing P-glycoprotein. Biochem Pharmacol. 1997 Jan 10;53(1):89-93. [PubMed:8960067 ]
Versantvoort CH, Rhodes T, Twentyman PR: Acceleration of MRP-associated efflux of rhodamine 123 by genistein and related compounds. Br J Cancer. 1996 Dec;74(12):1949-54. [PubMed:8980395 ]
Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]

Enzyme Details

3. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Imai Y, Tsukahara S, Asada S, Sugimoto Y: Phytoestrogens/flavonoids reverse breast cancer resistance protein/ABCG2-mediated multidrug resistance. Cancer Res. 2004 Jun 15;64(12):4346-52. [PubMed:15205350 ]
Zhang S, Yang X, Morris ME: Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport. Mol Pharmacol. 2004 May;65(5):1208-16. [PubMed:15102949 ]
Perez M, Real R, Mendoza G, Merino G, Prieto JG, Alvarez AI: Milk secretion of nitrofurantoin, as a specific BCRP/ABCG2 substrate, in assaf sheep: modulation by isoflavones. J Vet Pharmacol Ther. 2009 Oct;32(5):498-502. doi: 10.1111/j.1365-2885.2008.01050.x. [PubMed:19754918 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Showing metabocard for Genistein (HMDB0003217)

MOL for HMDB0003217 (Genistein)

3D MOL for HMDB0003217 (Genistein)

3D SDF for HMDB0003217 (Genistein)

3D-SDF for HMDB0003217 (Genistein)

PDB for HMDB0003217 (Genistein)

3D PDB for HMDB0003217 (Genistein)

SMILES for HMDB0003217 (Genistein)

INCHI for HMDB0003217 (Genistein)

Structure for HMDB0003217 (Genistein)

3D Structure for HMDB0003217 (Genistein)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

Reactions

References

References

References

References

Reactions

Transporters

References

References

References