NP-MRD: Showing NP-Card for Genistein (NP0000024)

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Record Information

Version

2.0

Created at

2006-05-22 15:12:42 UTC

Updated at

2024-09-03 04:17:07 UTC

NP-MRD ID

NP0000024

Natural Product DOI

https://doi.org/10.57994/0924

Secondary Accession Numbers

None

Natural Product 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


  Mrv1652306242117433D          

 30 32  0  0  0  0            999 V2000
    0.0835    0.3401   -1.7443 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5189    0.0272   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325   -0.0115    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8321    0.2859    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    1.0952    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8834    1.4039    0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5682    0.8951   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9089    1.2108   -0.4190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8773    0.0837   -1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5457   -0.2196   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168   -0.3504    1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.6291    1.9011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1626   -0.5995    0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4809   -0.8971    1.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4217   -0.8560    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7345   -1.1739    0.6675 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -0.5329   -1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7695   -0.2242   -1.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4934    0.0942   -2.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -0.2704   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9843    1.4873    1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3960    2.0498    1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4356    0.8544   -1.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4581   -0.3025   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -0.8505   -1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -0.4065    2.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -1.1528    2.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4902   -1.1700    0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557   -0.5091   -1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813    0.3289   -3.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  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
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20  2  1  0  0  0  0
 10  4  1  0  0  0  0
 20 13  1  0  0  0  0
  5 21  1  0  0  0  0
  6 22  1  0  0  0  0
  8 23  1  0  0  0  0
  9 24  1  0  0  0  0
 10 25  1  0  0  0  0
 11 26  1  0  0  0  0
 14 27  1  0  0  0  0
 16 28  1  0  0  0  0
 17 29  1  0  0  0  0
 19 30  1  0  0  0  0
M  END

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    0.0835    0.3401   -1.7443 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5189    0.0272   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325   -0.0115    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8321    0.2859    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    1.0952    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8834    1.4039    0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5682    0.8951   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9089    1.2108   -0.4190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8773    0.0837   -1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5457   -0.2196   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168   -0.3504    1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.6291    1.9011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1626   -0.5995    0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4809   -0.8971    1.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4217   -0.8560    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7345   -1.1739    0.6675 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -0.5329   -1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7695   -0.2242   -1.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4934    0.0942   -2.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -0.2704   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9843    1.4873    1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3960    2.0498    1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4356    0.8544   -1.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4581   -0.3025   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -0.8505   -1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -0.4065    2.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -1.1528    2.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4902   -1.1700    0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557   -0.5091   -1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813    0.3289   -3.0570 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


  Mrv1652306242117433D          

 30 32  0  0  0  0            999 V2000
    0.0835    0.3401   -1.7443 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5189    0.0272   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325   -0.0115    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8321    0.2859    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    1.0952    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8834    1.4039    0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5682    0.8951   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9089    1.2108   -0.4190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8773    0.0837   -1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5457   -0.2196   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168   -0.3504    1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.6291    1.9011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1626   -0.5995    0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4809   -0.8971    1.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4217   -0.8560    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7345   -1.1739    0.6675 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -0.5329   -1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7695   -0.2242   -1.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4934    0.0942   -2.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -0.2704   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9843    1.4873    1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3960    2.0498    1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4356    0.8544   -1.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4581   -0.3025   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -0.8505   -1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -0.4065    2.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -1.1528    2.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4902   -1.1700    0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557   -0.5091   -1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813    0.3289   -3.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  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
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20  2  1  0  0  0  0
 10  4  1  0  0  0  0
 20 13  1  0  0  0  0
  5 21  1  0  0  0  0
  6 22  1  0  0  0  0
  8 23  1  0  0  0  0
  9 24  1  0  0  0  0
 10 25  1  0  0  0  0
 11 26  1  0  0  0  0
 14 27  1  0  0  0  0
 16 28  1  0  0  0  0
 17 29  1  0  0  0  0
 19 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000024

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])OC2=C([H])C(O[H])=C([H])C(O[H])=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

$$$$

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    0.0835    0.3401   -1.7443 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5189    0.0272   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325   -0.0115    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8321    0.2859    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    1.0952    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8834    1.4039    0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5682    0.8951   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9089    1.2108   -0.4190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8773    0.0837   -1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5457   -0.2196   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168   -0.3504    1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.6291    1.9011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1626   -0.5995    0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4809   -0.8971    1.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4217   -0.8560    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7345   -1.1739    0.6675 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -0.5329   -1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7695   -0.2242   -1.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4934    0.0942   -2.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -0.2704   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9843    1.4873    1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3960    2.0498    1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4356    0.8544   -1.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4581   -0.3025   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -0.8505   -1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -0.4065    2.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -1.1528    2.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4902   -1.1700    0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557   -0.5091   -1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813    0.3289   -3.0570 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                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0       0.084   0.340  -1.744  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.519   0.027  -0.620  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.433  -0.012   0.379  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.832   0.286   0.153  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.555   1.095   1.006  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.883   1.404   0.830  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.568   0.895  -0.248  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.909   1.211  -0.419  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.877   0.084  -1.119  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.546  -0.220  -0.934  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.017  -0.350   1.645  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.243  -0.629   1.901  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.163  -0.600   0.974  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.481  -0.897   1.270  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.422  -0.856   0.269  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.734  -1.174   0.668  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.102  -0.533  -1.003  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.769  -0.224  -1.341  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.493   0.094  -2.628  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.837  -0.270  -0.323  0.00  0.00           C+0
HETATM   21  H   UNK     0      -1.984   1.487   1.858  0.00  0.00           H+0
HETATM   22  H   UNK     0      -4.396   2.050   1.542  0.00  0.00           H+0
HETATM   23  H   UNK     0      -6.436   0.854  -1.197  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.458  -0.303  -1.967  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.022  -0.851  -1.618  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.692  -0.407   2.491  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.734  -1.153   2.277  0.00  0.00           H+0
HETATM   28  H   UNK     0       6.490  -1.170   0.003  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.856  -0.509  -1.762  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.681   0.329  -3.057  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   23                                                       
CONECT    9    7   10   24                                                  
CONECT   10    9    4   25                                                  
CONECT   11    3   12   26                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   28                                                       
CONECT   17   15   18   29                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   30                                                       
CONECT   20   18    2   13                                                  
CONECT   21    5                                                            
CONECT   22    6                                                            
CONECT   23    8                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
CONECT   26   11                                                            
CONECT   27   14                                                            
CONECT   28   16                                                            
CONECT   29   17                                                            
CONECT   30   19                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    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

RDKit          3D

30 32  0  0  0  0  0  0  0  0999 V2000
    0.0835    0.3401   -1.7443 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5189    0.0272   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325   -0.0115    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8321    0.2859    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    1.0952    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8834    1.4039    0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5682    0.8951   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9089    1.2108   -0.4190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8773    0.0837   -1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5457   -0.2196   -0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168   -0.3504    1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.6291    1.9011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1626   -0.5995    0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4809   -0.8971    1.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4217   -0.8560    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7345   -1.1739    0.6675 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -0.5329   -1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7695   -0.2242   -1.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4934    0.0942   -2.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -0.2704   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9843    1.4873    1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3960    2.0498    1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4356    0.8544   -1.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4581   -0.3025   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -0.8505   -1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -0.4065    2.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -1.1528    2.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4902   -1.1700    0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557   -0.5091   -1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813    0.3289   -3.0570 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 DFT Assignments 3D Conformers

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 Mass

270.2400 Da

Monoisotopic Mass

270.05282 Da

IUPAC Name

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

Traditional Name

genistein

CAS Registry Number

446-72-0

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])OC2=C([H])C(O[H])=C([H])C(O[H])=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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, simulated)	V.dorna83			2021-09-07	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 200, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, simulated)	v.dorna83@yahoo.com	Not Available	Not Available	2021-07-19	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Acacia adunca	Plant	KNApSAcK
Acacia baileyana	Plant	KNApSAcK
Acacia binervata	Plant	KNApSAcK
Acacia calamifolia	Plant	KNApSAcK
Acacia cardiophylla	Plant	KNApSAcK
Acacia chrysotricha	Plant	KNApSAcK
Acacia clunies-rossiae	Plant	KNApSAcK
Acacia concurrens	Plant	KNApSAcK
Acacia constablei	Plant	KNApSAcK
Acacia cultriformis	Plant	KNApSAcK
Acacia dealbata	Plant	KNApSAcK
Acacia deanei	Plant	KNApSAcK
Acacia decurrens	Plant	KNApSAcK
Acacia elata	Plant	KNApSAcK
Acacia falciformis	Plant	KNApSAcK
Acacia filicifolia	Plant	KNApSAcK
Acacia fimbriata	Plant	KNApSAcK
Acacia holosericea	Plant	KNApSAcK
Acacia irrorata	Plant	KNApSAcK
Acacia kettlewelliae	Plant	KNApSAcK
Acacia lanigera	Plant	KNApSAcK
Acacia leucoclada	Plant	KNApSAcK
Acacia longifolia	Plant	KNApSAcK
Acacia mabellae	Plant	KNApSAcK
Acacia mearnsii	Plant	KNApSAcK
Acacia melanoxylon	Plant	KNApSAcK
Acacia mollifolia	Plant	KNApSAcK
Acacia neriifolia	Plant	KNApSAcK
Acacia obtusifolia	Plant	KNApSAcK
Acacia oshanesii	Plant	KNApSAcK
Acacia oswaldii	Plant	KNApSAcK
Acacia parramattensis	Plant	KNApSAcK
Acacia pycnantha	Plant	KNApSAcK
Acacia retinodes	Plant	KNApSAcK
Acacia rigens	Plant	KNApSAcK
Acacia silvestris	Plant	KNApSAcK
Acacia terminalis	Plant	KNApSAcK
Acacia trachyphloia	Plant	KNApSAcK
Acacia verniciflua	Plant	KNApSAcK
Acacia vestita	Plant	KNApSAcK
Achlys triphylla	LOTUS Database	35616633
Adenocarpus decorticans	Plant	KNApSAcK
Adenocarpus foliolosus	Plant	KNApSAcK
Allium sativum	FooDB	USDA
Aloe vera	Plant	KNApSAcK
Ammopiptanthus mongolicus	LOTUS Database	35616633
Amphicarpaea bracteata	Plant	KNApSAcK
Anacardium occidentale	FooDB	USDA
Anaxagorea luzonensis A.GRAY	Plant	KNApSAcK
Andira inermis	Plant	KNApSAcK
Apios americana	Plant	KNApSAcK
Apis mellifera	LOTUS Database	35616633
Arabidopsis thaliana	Plant	KNApSAcK
Arachis hypogaea	FooDB	PHENOL EXPLORER
Asparagus officinalis	FooDB	USDA
Astragalus verrucosus	LOTUS Database	35616633
Baptisia alba	Plant	KNApSAcK
Baptisia australis	Plant	KNApSAcK
Baptisia bracteata	Plant	KNApSAcK
Baptisia calycosa	Plant	KNApSAcK
Baptisia cinerea	Plant	KNApSAcK
Baptisia lanceolata	Plant	KNApSAcK
Baptisia lecontei	Plant	KNApSAcK
Baptisia megacarpa	Plant	KNApSAcK
Baptisia nuttalliana	Plant	KNApSAcK
Baptisia perfoliata	Plant	KNApSAcK
Baptisia tinctoria	Plant	KNApSAcK
Bolusanthus speciosus	LOTUS Database	35616633
Bos taurus	FooDB	USDA
Bowdichia nitida	Plant	KNApSAcK
Brassica oleracea	Plant	KNApSAcK
Brassica oleracea var. italica	FooDB	USDA
Bupleurum scorzonerifolium	Plant	KNApSAcK
Butea monosperma	LOTUS Database	35616633
Cajanus cajan	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cajanus scarabaeoides	Plant	KNApSAcK
Calicotome spinosa	Plant	KNApSAcK
Calicotome villosa	Plant	KNApSAcK
Calopogonium caeruleum	Plant	KNApSAcK
Camptosema rubicundum	Plant	KNApSAcK
Canavalia eurycarpa	Plant	KNApSAcK
Canavalia gladiata	Plant	KNApSAcK
Castanea sativa	FooDB	USDA
Chamaecytisus supinus	LOTUS Database	35616633
Cicer arietinum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus paradisi	FooDB	USDA
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	USDA
Cladrastis platycarpa	LOTUS Database	35616633
Clitoria falcata	Plant	KNApSAcK
Clitoria ternatea	Plant	KNApSAcK
Cocos nucifera	FooDB	USDA
Coffea arabica L.	FooDB	USDA
Coffea canephora	FooDB	USDA
Corylus	FooDB	USDA
Craspedolobium schochii	LOTUS Database	35616633
Crocus sativus	Plant	KNApSAcK
Crotalaria juncea	Plant	KNApSAcK
Crotalaria pallida	LOTUS Database	35616633
Crotalaria retusa	LOTUS Database	35616633
Crotalaria thebaica	LOTUS Database	35616633
Cudrania cochinchinensis var. gerontogea	Plant	KNApSAcK
Cullen corylifolium	Plant	KNApSAcK
Cytisus albus	Plant	KNApSAcK
Cytisus baeticus	Plant	KNApSAcK
Cytisus commutatus	Plant	KNApSAcK
Cytisus fontanesii	Plant	KNApSAcK
Cytisus monspessulanus L.	Plant	KNApSAcK
Cytisus proliferus	Plant	KNApSAcK
Cytisus ratisbonensis	Plant	KNApSAcK
Cytisus scoparius	Plant	KNApSAcK
Cytisus striatus	Plant	KNApSAcK
Dalbergia frutescens	LOTUS Database	35616633
Dalbergia odorifera	Plant	KNApSAcK
Dalbergia oliveri	LOTUS Database	35616633
Dalbergia parviflora	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633
Dermatophyllum secundiflorum	LOTUS Database	35616633
Desmodium gangeticum	Plant	KNApSAcK
Desmodium podocarpum	LOTUS Database	35616633
Desmodium uncinatum	Plant	KNApSAcK
Dipogon lignosus	Plant	KNApSAcK
Dunbaria villosa	Plant	KNApSAcK
Echinosophora koreensis	Plant	KNApSAcK
Echinospartum horridum	Plant	KNApSAcK
Erinacea anthyllis	Plant	KNApSAcK
Eriosema glomeratum	Plant	KNApSAcK
Eriosema nutans	Plant	KNApSAcK
Eriosema psoraleoides	Plant	KNApSAcK
Erycibe expansa	Plant	KNApSAcK
Erythrina burttii	Plant	KNApSAcK
Erythrina fusca	LOTUS Database	35616633
Erythrina latissima	Plant	KNApSAcK
Erythrina variegata	Plant	KNApSAcK
Erythroxylum ulei	Plant	KNApSAcK
Euchresta formosana	Plant	KNApSAcK
Fagelia bituminosa	-	KNApSAcK
Feijoa sellowiana	Plant	KNApSAcK
Ficus cordata	Plant	KNApSAcK
Ficus glumosa	LOTUS Database	35616633
Ficus nervosa	LOTUS Database	35616633
Ficus nymphaeifolia	Plant	KNApSAcK
Ficus pumila	LOTUS Database	35616633
Ficus septica	Plant	KNApSAcK
Flemingia macrophylla	Plant	KNApSAcK
Flemingia paniculata	LOTUS Database	35616633
Flemingia philippinensis	Plant	KNApSAcK
Flemingia stricta	Plant	KNApSAcK
Flemingia strobilifera	Plant	KNApSAcK
Galactia jussiaeana	Plant	KNApSAcK
Genista acanthoclada	Plant	KNApSAcK
Genista albida	Plant	KNApSAcK
Genista anglica	Plant	KNApSAcK
Genista canariensis	Plant	KNApSAcK
Genista cupanii	Plant	KNApSAcK
Genista depressa	Plant	KNApSAcK
Genista ephedroides	Plant	KNApSAcK
Genista hispanica	Plant	KNApSAcK
Genista hystrix	Plant	KNApSAcK
Genista linifolia	Plant	KNApSAcK
Genista lobelii	Plant	KNApSAcK
Genista microphylla	Plant	KNApSAcK
Genista morisii	Plant	KNApSAcK
Genista obtusiramea	Plant	KNApSAcK
Genista pulchella	Plant	KNApSAcK
Genista radiata	Plant	KNApSAcK
Genista sagittalis	Plant	KNApSAcK
Genista salzmannii	Plant	KNApSAcK
Genista scorpius	Plant	KNApSAcK
Genista sericea	Plant	KNApSAcK
Genista sessilifolia	Plant	KNApSAcK
Genista spartioides	Plant	KNApSAcK
Genista stenopetala	Plant	KNApSAcK
Genista subcapitata	Plant	KNApSAcK
Genista tinctoria	Plant	KNApSAcK
Genista triacanthos	Plant	KNApSAcK
Genista tricuspidata	LOTUS Database	35616633
Genista tridens	Plant	KNApSAcK
Genista tridentata	Plant	KNApSAcK
Genista ulicina	Plant	KNApSAcK
Glycine canescens	Plant	KNApSAcK
Glycine clandestina	Plant	KNApSAcK
Glycine falcata	Plant	KNApSAcK
Glycine latifolia	Plant	KNApSAcK
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Glycine tabacina	Plant	KNApSAcK
Glycine tomentella	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK
Halotydeus destructor	-	KNApSAcK
Hardenbergia violacea	Plant	KNApSAcK
Helianthus annuus L.	FooDB	PHENOL EXPLORER
Homo sapiens (Urine)	Animalia	KNApSAcK
Hordeum vulgare	FooDB	USDA
Hypericum scabrum	Plant	KNApSAcK
Ipomoea batatas	FooDB	USDA
Iris domestica	LOTUS Database	35616633
Iris pseudacorus	LOTUS Database	35616633
Juglans regia	FooDB	USDA
Kennedia coccinea	Plant	KNApSAcK
Kennedia nigricans	Plant	KNApSAcK
Kennedia procurrens	Plant	KNApSAcK
Kennedia rubicunda	Plant	KNApSAcK
Lablab purpureus	FooDB	KNAPSACK
Laburnum anagyroides	Plant	KNApSAcK
Lens culinaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lespedeza cyrtobotrya	Plant	KNApSAcK
Lespedeza floribunda	LOTUS Database	35616633
Lespedeza juncea	Plant	KNApSAcK
Linum usitatissimum	FooDB	USDA
Lonchocarpus utilis	LOTUS Database	35616633
Lupinus albus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lupinus angustifolius	LOTUS Database	35616633
Lupinus arboreus	Plant	KNApSAcK
Lupinus arcticus	Plant	KNApSAcK
Lupinus elegans	Plant	KNApSAcK
Lupinus luteus	Plant	KNApSAcK
Lupinus mexicanus	LOTUS Database	35616633
Lupinus mutabilis	Plant	KNApSAcK
Lupinus nanus	Plant	KNApSAcK
Lupinus pilosus	Plant	KNApSAcK
Lupinus pubescens	LOTUS Database	35616633
Lupinus sericeus	Plant	KNApSAcK
Lupinus subcarnosus	Plant	KNApSAcK
Lupinus texensis	Plant	KNApSAcK
Maackia amurensis	Plant	KNApSAcK
Maclura cochinchinensis	Plant	KNApSAcK
Maclura tricuspidata	LOTUS Database	35616633
Macroptilium bracteatum	Plant	KNApSAcK
Macroptilium lathyroides	Plant	KNApSAcK
Macroptilium martii	Plant	KNApSAcK
Medicago arabica	Plant	KNApSAcK
Medicago sativa	FooDB	KNAPSACK
Medicago truncatula	Plant	KNApSAcK
Millettia dielsiana	Plant	KNApSAcK
Moringa oleifera	Plant	KNApSAcK
Moringa peregrina	Plant	KNApSAcK
Moringa stenopetala	Plant	KNApSAcK
Mucuna pruriens	Plant	KNApSAcK
Neonotonia wightii	Plant	KNApSAcK
Neorautanenia amboensis	Plant	KNApSAcK
Olea europaea	FooDB	USDA
Ononis spinosa	Plant	KNApSAcK
Ophiocordyceps sinensis	LOTUS Database	35616633
Ormosia henryi	LOTUS Database	35616633
Ormosia monosperma	Plant	KNApSAcK
Oryza sativa	FooDB	USDA
Otholobium bolusii	Plant	KNApSAcK
Otholobium bracteolatum	Plant	KNApSAcK
Otholobium candicans	Plant	KNApSAcK
Otholobium hirtum	Plant	KNApSAcK
Otholobium spicatum	Plant	KNApSAcK
Otholobium striatum	Plant	KNApSAcK
Otholobium uncinatum	Plant	KNApSAcK
Otholobium wilmsii	Plant	KNApSAcK
Ougeinia dalbergioides	LOTUS Database	35616633
Passiflora edulis	FooDB	USDA
Pericopsis laxiflora	Plant	KNApSAcK
Phaseolus coccineus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus lunatus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phoenix dactylifera	FooDB	USDA
Piptanthus nepalensis	Plant	KNApSAcK
Piscidia piscipula	LOTUS Database	35616633
Pistacia vera	FooDB	USDA
Pisum sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Portulaca oleracea	LOTUS Database	35616633
Prumnopitys amara	LOTUS Database	35616633
Prunus armeniaca	FooDB	USDA
Prunus avium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus avium L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus cerasoides	LOTUS Database	35616633
Prunus cerasus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus domestica	FooDB	USDA
Prunus dulcis	FooDB	USDA
Prunus nipponica	LOTUS Database	35616633
Prunus serrulata	LOTUS Database	35616633
Prunus spp.	Plant	KNApSAcK
Pseudeminia comosa	Plant	KNApSAcK
Pseudoeriosema borianii	Plant	KNApSAcK
Pseudovigna argentea	Plant	KNApSAcK
Psoralea aculeata	Plant	KNApSAcK
Psoralea arborea	Plant	KNApSAcK
Psoralea axillaris	Plant	KNApSAcK
Psoralea effusa	Plant	KNApSAcK
Psoralea fascicularis	Plant	KNApSAcK
Psoralea laxa	Plant	KNApSAcK
Psoralea oligophylla	Plant	KNApSAcK
Psoralea repens	Plant	KNApSAcK
Pterocarpus angolensis	Plant	KNApSAcK
Pterocarpus marsupium	Plant	KNApSAcK
Pueraria candollei var. mirifica	Plant	KNApSAcK
Pueraria lobata	Plant	KNApSAcK
Pueraria mirifica	Plant	KNApSAcK
Pueraria montana	LOTUS Database	35616633
Pueraria montana var. lobata	Plant	KNApSAcK
Pueraria Phaseoloides	Plant	KNApSAcK
Pueraria tuberosa	Plant	KNApSAcK
Punica granatum	Plant	KNApSAcK
Retama monosperma	Plant	KNApSAcK
Retama raetam	Plant	KNApSAcK
Rhynchosia caribaea	Plant	KNApSAcK
Rhynchosia densiflora	Plant	KNApSAcK
Rhynchosia hirsuta	Plant	KNApSAcK
Rhynchosia phaseoloides	Plant	KNApSAcK
Rhynchosia pyramidalis	Plant	KNApSAcK
Ribes nigrum	FooDB	USDA
Sarcolobus globosus	-	KNApSAcK
Saussurea japonica	LOTUS Database	35616633
Securidaca inappendiculata	Plant	KNApSAcK
Slackia isoflavoniconvertens	-	KNApSAcK
Solanum tuberosum	FooDB	USDA
Solori scandens	Plant	KNApSAcK
Sophora alopecuroides	LOTUS Database	35616633
Sophora pachycarpa	LOTUS Database	35616633
Sophora secundiflora	Plant	KNApSAcK
Sophora subprostrata	Plant	KNApSAcK
Sophora tonkinensis	LOTUS Database	35616633
Sorbus cuspidata	LOTUS Database	35616633
Spartium junceum	LOTUS Database	35616633
Spatholobus suberectus	LOTUS Database	35616633
Spirotropis longifolia	LOTUS Database	35616633
Stemphilium sp. No. 644	-	KNApSAcK
Streptomyces globisporus	LOTUS Database	35616633
Streptomyces griseus	LOTUS Database	35616633
Streptomyces roseolus	LOTUS Database	35616633
Streptosporangium vulgare	LOTUS Database	35616633
Strongylodon macrobotrys	Plant	KNApSAcK
Styphnolobium japonicum	Plant	KNApSAcK
Syzygium jambos	LOTUS Database	35616633
Taxus fuana	Plant	KNApSAcK
Taxus wallichiana var. yunnanensis	Plant	KNApSAcK
Tephrosia toxicaria	Plant	KNApSAcK
Teyleria koordersii	Plant	KNApSAcK
Thermopsis alterniflora	Plant	KNApSAcK
Thermopsis lupinoides	LOTUS Database	35616633
Thermopsis macrophylla	Plant	KNApSAcK
Thermopsis mollis	Plant	KNApSAcK
Thermopsis montana	LOTUS Database	35616633
Thermopsis rhombifolia	Plant	KNApSAcK
Thermopsis villosa	Plant	KNApSAcK
Thunnus	FooDB	USDA
Thunnus alalunga	FooDB	USDA
Trifolium alpestre	LOTUS Database	35616633
Trifolium aureum	LOTUS Database	35616633
Trifolium campestre	Plant	KNApSAcK
Trifolium globosum	Plant	KNApSAcK
Trifolium medium	LOTUS Database	35616633
Trifolium pannonicum	Plant	KNApSAcK
Trifolium pratense	Plant	KNApSAcK
Trifolium repens	Plant	KNApSAcK
Trifolium riograndense	Plant	KNApSAcK
Trifolium spp.	Plant	KNApSAcK
Trifolium subterraneum	LOTUS Database	35616633
Trigonella foenum-graecum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Triticum	FooDB	USDA
Ulex boivinii	Plant	KNApSAcK
Ulex europaeus	Plant	KNApSAcK
Ulex gallii	Plant	KNApSAcK
Ulex genistoides	Plant	KNApSAcK
Ulex micranthus	Plant	KNApSAcK
Ulex minor	Plant	KNApSAcK
Ulex parviflorus	Plant	KNApSAcK
Vaccinium macrocarpon	FooDB	USDA
Vandasina retusa	Plant	KNApSAcK
Vicia faba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna angularis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna mungo	FooDB	KNAPSACK
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna subterranea	Plant	KNApSAcK
Vigna unguiculata ssp. unguiculata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vitis vinifera L.	FooDB	USDA
Wisteria brachybotrys	Plant	KNApSAcK
Zea mays	LOTUS Database	35616633
Zea mays L.	FooDB	KNAPSACK
Zingiber officinale	Plant	KNApSAcK

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 )

Physical Properties

State

Solid

Experimental 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

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

External Links

HMDB ID

HMDB0003217

DrugBank ID

DB01645

Phenol Explorer Compound ID

FoodDB 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

Good Scents ID

rw1504491

References

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 ]

Showing NP-Card for Genistein (NP0000024)

MOL for NP0000024 (Genistein)

3D MOL for NP0000024 (Genistein)

3D SDF for NP0000024 (Genistein)

3D-SDF for NP0000024 (Genistein)

PDB for NP0000024 (Genistein)

3D PDB for NP0000024 (Genistein)

SMILES for NP0000024 (Genistein)

INCHI for NP0000024 (Genistein)

Structure for NP0000024 (Genistein)

3D Structure for NP0000024 (Genistein)