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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:58:14 UTC
Update Date2019-07-23 06:29:45 UTC
HMDB IDHMDB0039489
Secondary Accession Numbers
  • HMDB39489
Metabolite Identification
Common Name6''-O-Acetylglycitin
Description6''-O-Acetylglycitin, also known as glycitin 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. 6''-O-Acetylglycitin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 6''-O-Acetylglycitin is found, on average, in the highest concentration within a few different foods, such as soy beans, other soy products, and soy milks and in a lower concentration in soy sauces, tofus, and miso. 6''-O-Acetylglycitin has also been detected, but not quantified in, pulses. This could make 6''-O-acetylglycitin a potential biomarker for the consumption of these foods. A glycosyloxyisoflavone that is glycitin carrying an acetyl substituent at position 6 on the glucose moiety.
Structure
Data?1563863385
Synonyms
ValueSource
7,4'-Dihydroxy-6-methoxyisoflavone 7-O-(6''-acetylglucoside)ChEBI
AcetylglycitinChEBI
Glycitein 6''-O-acetylglucosideChEBI
Glycitein 7-(6-O-acetyl-beta-D-glucopyranoside)ChEBI
Glycitein 7-O-beta-D-(6''-O-acetyl)glucopyranosideChEBI
Glycitein 7-O-beta-D-(6''-O-acetyl)glucosideChEBI
Glycitin 6''-O-acetateChEBI
Glycitein 7-(6-O-acetyl-b-D-glucopyranoside)Generator
Glycitein 7-(6-O-acetyl-β-D-glucopyranoside)Generator
Glycitein 7-O-b-D-(6''-O-acetyl)glucopyranosideGenerator
Glycitein 7-O-β-D-(6''-O-acetyl)glucopyranosideGenerator
Glycitein 7-O-b-D-(6''-O-acetyl)glucosideGenerator
Glycitein 7-O-β-D-(6''-O-acetyl)glucosideGenerator
Glycitin 6''-O-acetic acidGenerator
6''-O-AcetylglycitinChEBI
Glycitein 7-(6-O-acetyl-b-D-glucoside)Generator
Glycitein 7-(6-O-acetyl-β-D-glucoside)Generator
Chemical FormulaC24H24O11
Average Molecular Weight488.4408
Monoisotopic Molecular Weight488.13186161
IUPAC Name[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-6-methoxy-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl acetate
Traditional Name[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-6-methoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl acetate
CAS Registry Number134859-96-4
SMILES
COC1=CC2=C(OC=C(C2=O)C2=CC=C(O)C=C2)C=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C24H24O11/c1-11(25)32-10-19-21(28)22(29)23(30)24(35-19)34-18-8-16-14(7-17(18)31-2)20(27)15(9-33-16)12-3-5-13(26)6-4-12/h3-9,19,21-24,26,28-30H,10H2,1-2H3/t19-,21-,22+,23-,24-/m1/s1
InChI KeyDUBPGEJGGVZKDD-PFKOEMKTSA-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-7-o-glycoside
  • Isoflavone
  • Phenolic glycoside
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Pyran
  • Oxane
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Secondary alcohol
  • Polyol
  • Acetal
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point155 - 157 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP1.41ALOGPS
logP0.75ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.96ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area161.21 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity117.46 m³·mol⁻¹ChemAxon
Polarizability48.5 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abc-6323900000-1087024aa60fb94fecc5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-066r-9431048000-e74ad95ef5db8191d834Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1080900000-b4cb6f070b27956e627dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090100000-2060d8610dbcd0df2e0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-2190000000-68f0eddd5ed04ef67654Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a5i-9140600000-25c6a64b4fd889c8ed38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-9070200000-69a3ab4d3fe827ae5c81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0apl-6090000000-87aed3525c506d814660Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID406
FooDB IDFDB019095
KNApSAcK IDC00019122
Chemspider ID8403585
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10228095
PDB IDNot Available
ChEBI ID133348
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .