MiMeDB: Showing metabocard for Genistein (MMDBc0000420)

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:21 UTC

Update Date

2022-08-31 06:06:51 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

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

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

Tissue Locations

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

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191713	Nuclear receptor coactivator 1	Enzyme	Q15788	Homo_sapiens
MMDBp0191749	Dehydrogenase/reductase SDR family member 4	Enzyme	Q9BTZ2	Homo_sapiens
MMDBp0192112	Estrogen receptor beta	Enzyme	Q92731	Homo_sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo_sapiens
MMDBp0192992	Protein-tyrosine kinase 2-beta	Unknown	Q14289	Homo_sapiens
MMDBp0193115	Cytochrome P450 1A2	Unknown	P05177	Homo_sapiens
MMDBp0193300	Multidrug resistance-associated protein 1	Transporter	P33527	Homo_sapiens
MMDBp0193411	Estrogen receptor	Enzyme	P03372	Homo_sapiens
MMDBp0193419	Multidrug resistance protein 1	Transporter	P08183	Homo_sapiens
MMDBp0193475	ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	Homo_sapiens
MMDBp0196283	DNA topoisomerase 2-alpha	Enzyme	P11388	Homo_sapiens
MMDBp0197061	Sulfotransferase 1A3	Enzyme	P0DMM9	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Ileostomy	Increased	Association	Human Urine	HMDB	17413104

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1		Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

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

HMDB ID

HMDB0003217

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

CMMC Knowledgebase

Not Available

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 ]
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. doi: 10.1016/j.lfs.2003.04.006. [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. doi: 10.1016/j.mce.2004.03.011. [PubMed:15196699 ]
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. doi: 10.1016/j.neuro.2003.11.001. [PubMed:15288519 ]
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. doi: 10.1097/00042192-200512020-00013. [PubMed:15772566 ]
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. doi: 10.1158/0008-5472.CAN-04-2807. [PubMed:15833883 ]
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. doi: 10.1021/jf0484024. [PubMed:15853412 ]
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. doi: 10.1158/0008-5472.CAN-04-4604. [PubMed:16061678 ]
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. doi: 10.1016/j.jnutbio.2005.04.008. [PubMed:16109484 ]
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Showing metabocard for Genistein (MMDBc0000420)

MOL for #<Metabolite:0x00007f12412d6bf8>

3D MOL for #<Metabolite:0x00007f12412d6bf8>

3D SDF for #<Metabolite:0x00007f12412d6bf8>

3D-SDF for #<Metabolite:0x00007f12412d6bf8>

PDB for #<Metabolite:0x00007f12412d6bf8>

3D PDB for #<Metabolite:0x00007f12412d6bf8>

SMILES for #<Metabolite:0x00007f12412d6bf8>

INCHI for #<Metabolite:0x00007f12412d6bf8>

Structure for #<Metabolite:0x00007f12412d6bf8>

3D Structure for #<Metabolite:0x00007f12412d6bf8>