MiMeDB: Showing metabocard for Genistein (MMDBc0000420)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:21 UTC

Update Date

2024-09-27 19:47:36 UTC

Metabolite ID

MMDBc0000420

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>
MMDBc0000420

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₅H₁₀O₅

Average Mass

270.24

Monoisotopic Mass

270.052823422

IUPAC Name

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

Traditional Name

genistein

CAS Registry Number

Not Available

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

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-0321900000-1dd6fcaf99898bd949df	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0321900000-1dd6fcaf99898bd949df	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0490000000-2922d094b504ca63625f	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00di-3232900000-5532bb09d0ee2a1c2b07	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-014l-9600000000-04b546320e268d817276	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00kf-5910000000-7e265d1b4640f882195a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0v4m-1960000000-7843ec8ae23314f88147	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0290000000-52ec910b223a3688fbc0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0190000000-4045f471e10774927fb0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0090000000-b593f863241cb83cbaa8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0190000000-0cd8d123608bd54f7214	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-00di-0090000000-9ce354d07dc39313259b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0910000000-5eb75a138568fa4ac897	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0fr6-2920000000-a32f6ae97952bb96de05	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-0290000000-4592d557e739a114cbfa	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive	splash10-00di-0090000000-14ae481944ad1a1f7ca0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-014i-0090030000-a3400b0a77da6983528f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-6db4d2441911d696b121	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-6db4d2441911d696b121	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-001i-0900000000-ad50062f85b9c32e1426	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-001i-0910000000-6a694e60823635f66757	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-720c4e1f43db9f50b589	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-0e3ca66534f635efb4d8	2017-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-3ca72bf3c489e8b06845	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0090000000-664850196c63c1380b4e	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-5790000000-f3cf7e73e69ebaba0989	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-aa4506f67fa71b5e6f4e	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-f1f0ad0b45f461f988db	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gb9-3960000000-16725698ad6eee8f88dc	2017-06-28	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)		2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)		2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		2012-12-05	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.39	0.18			umol/mmol creatinine	Adult (>18 years old)	Both	Soy consumption (ileostomies)	HMDB	17413104
Human Urine	Detected and Quantified	0.00122				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19167951
Human Blood	Detected and Quantified	0.0027				uM	Adult (>18 years old)	Female	Normal	HMDB	20332276
Human Blood	Detected and Quantified	0.0057				uM	Adult (>18 years old)	Female	Normal	HMDB	9796633
Human Blood	Detected and Quantified	0.00925				uM	Adult (>18 years old)	Female	Normal	HMDB	9796633
Human Urine	Detected and Quantified	0.00971				umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	HMDB	17976571
Human Blood	Detected and Quantified	0.0122				uM	Adult (>18 years old)	Female	Normal	HMDB	12600860
Human Urine	Detected and Quantified	0.0124				umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	20332276
Human Blood	Detected and Quantified	0.013				uM	Adult (>18 years old)	Female	Normal	HMDB	15159299
Human Urine	Detected and Quantified	0.0147				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Blood	Detected and Quantified	0.0169				uM	Adult (>18 years old)	Both	Normal	HMDB	12396157
Human Urine	Detected and Quantified	0.0185				umol/mmol creatinine	Children (1 - 13 years old)	Female	Normal	HMDB	17366830
Human Blood	Detected and Quantified	0.0278				uM	Adult (>18 years old)	Female	Normal	HMDB	11570994
Human Urine	Detected and Quantified	0.0292				umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	15159299
Human Blood	Detected and Quantified	0.0338				uM	Adult (>18 years old)	Male	Normal	HMDB	16205743
Human Blood	Detected and Quantified	0.0588				uM	Adult (>18 years old)	Female	Normal	HMDB	11570994
Human Urine	Detected and Quantified	0.0907				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	18469267
Human Urine	Detected and Quantified	0.18				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15005831
Human Blood	Detected and Quantified	0.181				uM	Adult (>18 years old)	Female	Normal	HMDB	10778038
Human Urine	Detected and Quantified	0.193				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	18469267
Human Urine	Detected and Quantified	0.215				umol/mmol creatinine	Children (1-13 years old)	Female	Normal	HMDB	20385037
Human Blood	Detected and Quantified	0.246				uM	Adult (>18 years old)	Both	Normal	HMDB	15005831
Human Urine	Detected and Quantified	0.272				umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	22493748
Human Blood	Detected and Quantified	0.278				uM	Adult (>18 years old)	Female	Normal	HMDB	10778038
Human Blood	Detected and Quantified	0.285				uM	Adult (>18 years old)	Female	Normal	HMDB	11570994
Human Blood	Detected and Quantified	0.525				uM	Adult (>18 years old)	Female	Normal	HMDB	11570994
Human Urine	Detected and Quantified	0.644				umol/mmol creatinine	Children (1-13 years old)	Female	Normal	HMDB	20385037
Human Urine	Detected and Quantified	0.707				umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	10778038
Human Urine	Detected and Quantified	0.753				umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	10778038
Human Blood	Detected and Quantified	0.00022	0.00030			uM	Adult (>18 years old)	Both	Normal	HMDB	9618027
Human Blood	Detected and Quantified	0.0063		0.0056	0.0071	uM	Adult (>18 years old)	Female	Normal	HMDB	17449595
Human Blood	Detected and Quantified	0.0065		0.0057	0.0074	uM	Adult (>18 years old)	Male	Normal	HMDB	17449595
Human Urine	Detected and Quantified	0.0140	0.0133			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	10744130
Human Urine	Detected and Quantified	0.0160	0.0200			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	10744130
Human Blood	Detected and Quantified	0.0183	0.0207			uM	Adult (>18 years old)	Female	Normal	HMDB	15623842
Human Urine	Detected and Quantified	0.0192	0.0272			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	9681530
Human Urine	Detected and Quantified	0.0237	0.0300			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Blood	Detected and Quantified	0.025		0.000	0.050	uM	Adult (>18 years old)	Both	Normal	HMDB	9618027
Human Urine	Detected and Quantified	0.028		0.0077	0.064	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	0.032	0.007			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	10822017
Human Urine	Detected and Quantified	0.0352	0.0560			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	9681530
Human Urine	Detected and Quantified	0.0367	0.0813			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	10744130
Human Urine	Detected and Quantified	0.0448	0.0992			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	9681530
Human Urine	Detected and Quantified	0.0571	0.0674			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	18791925
Human Urine	Detected and Quantified	0.104	0.168			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	9681530
Human Urine	Detected and Quantified	0.105	0.199			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	18791925
Human Urine	Detected and Quantified	0.11	0.017			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	10822017
Human Urine	Detected and Quantified	0.115	0.259			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	9681530
Human Urine	Detected and Quantified	0.200	0.320			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	17353586
Human Urine	Detected and Quantified	0.214	0.298			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	9681530
Human Urine	Detected and Quantified	0.23	0.08			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	17413104
Human Blood	Detected and Quantified	0.307	0.325			uM	Adult (>18 years old)	Female	Normal	HMDB	10778038
Human Blood	Detected and Quantified	0.475	0.510			uM	Adult (>18 years old)	Both	Normal	HMDB	11584098
Human Urine	Detected and Quantified	0.880	0.693			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	10778038
Human Urine	Detected and Quantified	0.947	0.940			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	11584098
Human Urine	Detected and Quantified	0.0127		0.0108	0.0150	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2013
Human Urine	Detected and Quantified	0.0228		0.0174	0.0251	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2013
Human Urine	Detected and Quantified			0.26	0.46	umol/mmol creatinine	Not Specified	Both	Genistein Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.16	0.21	umol/mmol creatinine	Not Specified	Both	Genistein Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.19	0.47	umol/mmol creatinine	Not Specified	Both	Genistein Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.16	0.26	umol/mmol creatinine	Not Specified	Both	Genistein Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.17	0.31	umol/mmol creatinine	Not Specified	Both	Genistein Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.14	0.21	umol/mmol creatinine	Not Specified	Both	Genistein Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23657156
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

References

General References

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. doi: 10.1006/excr.2000.4914. [PubMed:10912792 ]
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. doi: 10.1097/01.ju.0000046780.23389.e0. [PubMed:12629420 ]
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Showing metabocard for Genistein (MMDBc0000420)

MOL for #<Metabolite:0x00007fb7b460d588>

3D MOL for #<Metabolite:0x00007fb7b460d588>

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Structure for #<Metabolite:0x00007fb7b460d588>

3D Structure for #<Metabolite:0x00007fb7b460d588>