Record Information
Version1.0
Creation date2010-04-08 22:04:40 UTC
Update date2018-05-29 18:26:31 UTC
Primary IDFDB000669
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6''-O-Acetylgenistin
Description(3,4,5-Trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetate, also known as 6"-O-acetylgenistin or genistin 6''-O-acetate, 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 (3,4,5-Trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetate exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule (3,4,5-Trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetate 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, miso, and tofus (3,4,5-Trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetate has also been detected, but not quantified in, pulses and soy sauces. This could make (3,4,5-trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetate a potential biomarker for the consumption of these foods.
CAS Number73566-30-0
Structure
Thumb
Synonyms
SynonymSource
(3,4,5-Trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetic acidGenerator
6"-O-acetylgenistinHMDB
6'-O-AcetylgenistinHMDB
6-O-AcetylgenistinHMDB
Genistin 6''-O-acetateHMDB
6-o-acetylgenistinbiospider
6''-O-Acetylgenistindb_source
6"-O-Acetylgenistinbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.48 g/LALOGPS
logP1.25ALOGPS
logP1.25ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.27ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area172.21 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity112.98 m³·mol⁻¹ChemAxon
Polarizability46.22 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC23H22O11
IUPAC name(3,4,5-trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetate
InChI IdentifierInChI=1S/C23H22O11/c1-10(24)31-9-17-20(28)21(29)22(30)23(34-17)33-13-6-15(26)18-16(7-13)32-8-14(19(18)27)11-2-4-12(25)5-3-11/h2-8,17,20-23,25-26,28-30H,9H2,1H3
InChI KeyDXWGBJJLEDQBKS-UHFFFAOYSA-N
Isomeric SMILESCC(=O)OCC1OC(OC2=CC(O)=C3C(OC=C(C3=O)C3=CC=C(O)C=C3)=C2)C(O)C(O)C1O
Average Molecular Weight474.418
Monoisotopic Molecular Weight474.116211528
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 o-glycoside
  • Isoflavonoid-7-o-glycoside
  • Isoflavone
  • Hydroxyisoflavonoid
  • Phenolic glycoside
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Acetal
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.23%; H 4.67%; O 37.10%DFC
Melting PointMp 185-186°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-7420900000-399a71205fed850564aeJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00b9-3011109000-ddbd2141b60ef4377b38JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1090800000-10a4e5d5b1465d78b93fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090100000-d77e656717aa9832caafJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-3290000000-7607b39523fdee892d23JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0avi-9140600000-74df749bf00668a5fd31JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-9070100000-53ea2181f3aac4092c1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-7190000000-6f1261b04e21d9e7afd4JSpectraViewer
ChemSpider ID11317869
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID22288010
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID405
DrugBank IDNot Available
HMDB IDHMDB29528
CRC / DFC (Dictionary of Food Compounds) IDGZR02-N:BFL71-Q
EAFUS IDNot Available
Dr. Duke ID6"-O-ACETYL-GENISTIN
BIGG IDNot Available
KNApSAcK IDC00010104
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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.