Showing metabocard for Genistein (BMDB0003217)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:03:08 UTC
Update Date2020-06-04 20:47:26 UTC
BMDB IDBMDB0003217
Secondary Accession Numbers
  • BMDB03217
Metabolite 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 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Genistein is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
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
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
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
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Gland
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Milk
  • Neuron
  • Placenta
  • Platelet
  • Prostate Tissue
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified0.000370 - 0.00740 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.0148 - 0.107 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified9.51 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified11.175 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.438 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.0679 uMNot SpecifiedNot Specified
Normal		 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003217
DrugBank IDDB01645
Phenol Explorer Compound ID396
FooDB 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
Synthesis ReferenceBaker, Wilson; Robinson, Robert. Synthetical experiments in the isoflavone group. IV. Synthesis of 2-methylirigenol. Journal of the Chemical Society (1929), Volume Date 1928, 152-61.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. King RA, Mano MM, Head RJ: Assessment of isoflavonoid concentrations in Australian bovine milk samples. J Dairy Res. 1998 Aug;65(3):479-89. [PubMed:9718497 ]
  2. Antignac JP, Cariou R, Le Bizec B, Cravedi JP, Andre F: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(12):1256-64. doi: 10.1002/rcm.1052. [PubMed:12811748 ]
  3. Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. [PubMed:18565930 ]