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Record Information
Version1.0
Created at2006-05-22 15:12:42 UTC
Updated at2020-09-11 01:32:46 UTC
NP-MRD IDNP0000024
Secondary Accession NumbersNone
Natural Product Identification
Common NameGenistein
DescriptionGenistein, also known as prunetol or sophoricol, 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. Thus, genistein is considered to be a flavonoid lipid molecule. Genistein is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Genistein is a bitter tasting compound. Outside of the human body, Genistein is found, on average, in the highest concentration within a few different foods, such as lima beans, soy beans, and natto and in a lower concentration in blackcurrants, black-eyed pea, and other soy products. Genistein has also been detected, but not quantified in, several different foods, such as wild celeries, chinese cabbages, butternut squash, rapes, and evergreen huckleberries. This could make genistein a potential biomarker for the consumption of these foods. Genistein is a potentially toxic compound. 7-Hydroxyisoflavone with additional hydroxy groups at positions 5 and 4'.
Structure
Thumb
Synonyms
ValueSource
4',5,7-TrihydroxyisoflavoneChEBI
5,7,4'-TrihydroxyisoflavoneChEBI
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
PrunetolChEBI
SophoricolChEBI
4',5, 7-TrihydroxyisoflavoneHMDB
4',5,7-Trihydroxy-isoflavoneHMDB
4,5,7-Trihydroxy iso-flavoneHMDB
Genistein 85% HPLCHMDB
GenisteolHMDB
GenisterinHMDB
GenesteinHMDB
Chemical FormulaC15H10O5
Average Molecular Weight270.24
Monoisotopic Molecular Weight270.052823422
IUPAC Name5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Namegenistein
CAS Registry Number446-72-0
SMILES
OC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O
InChI Identifier
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
InChI KeyTZBJGXHYKVUXJN-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumJSpectraViewer
Species of Origin
SpeciesAnimalia; Plantae
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflav-2-enes
Direct ParentIsoflavones
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point301.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP3.04ALOGPS
logP3.08ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.55ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.68 m³·mol⁻¹ChemAxon
Polarizability26.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0003217
DrugBank IDDB01645
Phenol Explorer Compound ID396
FoodDB IDFDB011828
KNApSAcK IDC00002526
Chemspider ID4444448
KEGG Compound IDC06563
BioCyc IDCPD-3141
BiGG IDNot Available
Wikipedia LinkGenistein
METLIN ID3398
PubChem Compound5280961
PDB IDNot Available
ChEBI ID28088
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. Si H, Liu D: Phytochemical genistein in the regulation of vascular function: new insights. Curr Med Chem. 2007;14(24):2581-9. [PubMed:17979711 ]
  14. 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 ]