Genistein 4'-O-glucuronide (CHEM041608)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:35:19 UTC
Update Date2016-11-09 01:22:30 UTC
Accession NumberCHEM041608
Identification
Common NameGenistein 4'-O-glucuronide
ClassSmall Molecule
DescriptionGenistein 4'-O-glucuronide is a polyphenol metabolite detected in biological fluids (PMID: 20428313).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,3S,4S,5R,6S)-6-[4-(5,7-Dihydroxy-4-oxo-4H-chromen-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylateHMDB
Chemical FormulaC21H18O11
Average Molecular Mass446.361 g/mol
Monoisotopic Mass446.085 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxochromen-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILESO[C@@H]1[C@@H](O)[C@H](OC2=CC=C(C=C2)C2=COC3=C(C(O)=CC(O)=C3)C2=O)O[C@@H]([C@H]1O)C(O)=O
InChI IdentifierInChI=1S/C21H18O11/c22-9-5-12(23)14-13(6-9)30-7-11(15(14)24)8-1-3-10(4-2-8)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21-23,25-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1
InChI KeyNHEBJNCJBWUPCK-ZFORQUDYSA-N
Chemical Taxonomy
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 o-glycoside
  • Isoflavonoid-4p-o-glycoside
  • Isoflavone
  • Hydroxyisoflavonoid
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Phenoxy compound
  • Phenol ether
  • Pyranone
  • Beta-hydroxy acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.05 g/LALOGPS
logP0.99ALOGPS
logP1.13ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area183.21 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.69 m³·mol⁻¹ChemAxon
Polarizability42.04 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9114300000-2defebabeba59940cb40Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-006t-3053159000-a0296158d434b9e0ac02Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-0070900000-60a833d89157be95e9d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090100000-42562115265c5f0bc08eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-2590000000-d131d04b2bd84223ce2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-0141900000-7c7edb9ac51f3ffa3a7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1191200000-f81e3f05accfd5277dfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-2190000000-6de456fa9bf91aa4f4a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0020900000-a85515efc7a5cf1c4c29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-024i-0258900000-a1b01d7dd0b3d44cf875Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-2293100000-eae74b9227c7a9768d57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004j-0220900000-c817cac6300d4c70790bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-5295400000-c49d0599bbc19aca7230Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-2090000000-756383b962e46c1e2576Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0041737
FooDB IDFDB029904
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID29813968
ChEBI IDNot Available
PubChem Compound ID45782816
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8.