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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:34:46 UTC
Update Date2019-07-23 06:23:34 UTC
HMDB IDHMDB0037342
Secondary Accession Numbers
  • HMDB37342
Metabolite Identification
Common NameApigenin 7-O-(6''-O-acetylglucoside)
DescriptionApigenin 7-O-(6''-O-acetylglucoside) belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Apigenin 7-O-(6''-O-acetylglucoside) is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Apigenin 7-O-(6''-O-acetylglucoside) has been detected, but not quantified in, german camomiles and herbs and spices. This could make apigenin 7-O-(6''-O-acetylglucoside) a potential biomarker for the consumption of these foods.
Structure
Data?1563863014
Synonyms
ValueSource
Apigenin 7-(6''-acetylglucoside)HMDB
(3,4,5-Trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetic acidGenerator
Chemical FormulaC23H22O11
Average Molecular Weight474.4142
Monoisotopic Molecular Weight474.116211546
IUPAC Name(3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetate
Traditional Name(3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl)methyl acetate
CAS Registry Number72741-92-5
SMILES
CC(=O)OCC1OC(OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)C(O)C(O)C1O
InChI Identifier
InChI=1S/C23H22O11/c1-10(24)31-9-18-20(28)21(29)22(30)23(34-18)32-13-6-14(26)19-15(27)8-16(33-17(19)7-13)11-2-4-12(25)5-3-11/h2-8,18,20-23,25-26,28-30H,9H2,1H3
InChI KeyLYFXRHUNCZZUTQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Oxane
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP1.26ALOGPS
logP0.88ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)8.31ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area172.21 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity114.21 m³·mol⁻¹ChemAxon
Polarizability46.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9432800000-728924c6ae638062ab33Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-5410009000-2916e20658879c138010Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1080900000-0c7e6f20670726ade021Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090100000-a63d5a022830472ac66dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-3290000000-3f8dbc6343efb6f39b91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0avi-9140600000-ec337103cf163b188dacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-9070100000-d95a867a64ebbb53bcb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-7190000000-1433420bee7d98479faaSpectrum
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 IDNot Available
FooDB IDFDB016364
KNApSAcK IDC00004177
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14325222
PDB IDNot Available
ChEBI IDNot Available
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.. .