Record Information
Version1.0
Creation date2010-04-08 22:10:03 UTC
Update date2018-05-28 23:35:04 UTC
Primary IDFDB012221
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGenistin
DescriptionGenistin, also known as genistin (8ci) or genistoside, belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Genistin is an extremely weak basic (essentially neutral) compound (based on its pKa). Genistin is a bitter tasting compound. Genistin is found, on average, in the highest concentration in a few different foods, such as soy beans, soy yogurts, and other soy products and in a lower concentration in soy milks, soy sauces, and miso. Genistin has also been detected, but not quantified in, several different foods, such as kales, chinese cabbages, endives, orange bell peppers, and ucuhuba. This could make genistin a potential biomarker for the consumption of these foods.
CAS Number529-59-9
Structure
Thumb
Synonyms
SynonymSource
4',5,7-Trihydroxyisoflavone 7-D-glucosideHMDB
4',5,7-Trihydroxyisoflavone 7-glucosideHMDB
Genistein 7-glucosideHMDB
Genistein 7-O-beta-D-glucosideHMDB
Genistein glucosideHMDB
Genistein, 7-beta-D-glucopyranosideHMDB
Genistein, 7-O-beta-D-glucosideHMDB
Genistein-7-glucosideHMDB
Genistein-7-O-beta-D-glucopyranosideHMDB
Genistein-7beta-D-glucopyranosideHMDB
Genisteol 7-monoglucosideHMDB
Genistin (8ci)HMDB
GenistineHMDB
GenistosideHMDB
Glucosyl-7-genisteinHMDB
Isoflavone, 4',5,7-trihydroxy-, 7-D-glucosideHMDB
Prevention 10 (soy isoflavone concentrate)HMDB
4',5,7-trihydroxyisoflavone 7-D-glucosidebiospider
Genistindb_source
Genistin (8CI)biospider
Glucopyranoside, genistein-7, beta-D-biospider
Predicted Properties
PropertyValueSource
Water Solubility1.01 g/LALOGPS
logP0.68ALOGPS
logP0.81ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.36ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.83 m³·mol⁻¹ChemAxon
Polarizability42.18 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H20O10
IUPAC name5-hydroxy-3-(4-hydroxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
InChI IdentifierInChI=1S/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2
InChI KeyZCOLJUOHXJRHDI-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=CC(O)=C3C(=O)C(=COC3=C2)C2=CC=C(O)C=C2)C(O)C(O)C1O
Average Molecular Weight432.3775
Monoisotopic Molecular Weight432.10564686
Classification
Description belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavonoid O-glycosides
Direct ParentIsoflavonoid O-glycosides
Alternative Parents
Substituents
  • Isoflavonoid-7-o-glycoside
  • Isoflavonoid o-glycoside
  • Isoflavone
  • Hydroxyisoflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • an isoflavone-7-O-β-D-glucoside (CPD-3421 )
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.34%; H 4.66%; O 37.00%DFC
Melting PointMp 254-256° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]21D -27.7 (MeOH aq.)DFC
Spectroscopic UV Data[neutral] lmax 262 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0h9r-8914800000-b5711d35ff3a85cfffaeJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001r-3620009000-a32e57795ebbf7519666JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-0190800000-9dd0f3e25b5de14320ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-7ac795a53e2622d6fa04JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ukc-2190000000-c75c9f5db7ba30e7d39bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-0151900000-5143ebb19841b93ba06fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1090200000-48a472ce7e9a2884d653JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3290000000-caa3fe4a15ea8a74bf71JSpectraViewer
ChemSpider ID4447683
ChEMBL IDNot Available
KEGG Compound IDC09126
Pubchem Compound ID5284639
Pubchem Substance IDNot Available
ChEBI ID27514
Phenol-Explorer ID404
DrugBank IDNot Available
HMDB IDHMDB33988
CRC / DFC (Dictionary of Food Compounds) IDGZR02-N:HFF90-F
EAFUS IDNot Available
Dr. Duke IDGENISTIN
BIGG IDNot Available
KNApSAcK IDC00002528
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGenistein_7-glucoside
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
estrogenicDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.