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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:07:04 UTC
Update Date2019-07-23 06:13:20 UTC
HMDB IDHMDB0033399
Secondary Accession Numbers
  • HMDB33399
Metabolite Identification
Common NameAnnocherin A
DescriptionQuercetin 3-(6''''-feruloylglucosyl)-(1->2)-galactosyl-(1->2)-glucoside belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Quercetin 3-(6''''-feruloylglucosyl)-(1->2)-galactosyl-(1->2)-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Quercetin 3-(6''''-feruloylglucosyl)-(1->2)-galactosyl-(1->2)-glucoside has been detected, but not quantified in, pulses. This could make quercetin 3-(6''''-feruloylglucosyl)-(1->2)-galactosyl-(1->2)-glucoside a potential biomarker for the consumption of these foods.
Structure
Data?1563862400
Synonyms
ValueSource
3-[[O-6-O-[(2E)-3-(4-Hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]-beta-D-glucopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneHMDB
{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetic acidGenerator
Chemical FormulaC24H38O5
Average Molecular Weight406.5555
Monoisotopic Molecular Weight406.271924326
IUPAC Name{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate
Traditional Name{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate
CAS Registry Number218281-62-0
SMILES
CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(COC(C)=O)C1CC3
InChI Identifier
InChI=1S/C24H38O5/c1-16(25)28-14-21(3)9-5-10-22(4)19(21)8-11-23-12-18(6-7-20(22)23)24(27,13-23)15-29-17(2)26/h18-20,27H,5-15H2,1-4H3
InChI KeyOQDCKOUFTOKDOD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Oligosaccharide
  • Flavonoid-3-o-glycoside
  • Flavone
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Methoxyphenol
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Anisole
  • Catechol
  • Styrene
  • Alkyl aryl ether
  • Fatty acid ester
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Oxane
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Heteroaromatic compound
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Ether
  • Polyol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

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 Solubility0.0024 g/LALOGPS
logP3.54ALOGPS
logP3.2ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)13.75ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity109.17 m³·mol⁻¹ChemAxon
Polarizability46.29 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, Positivesplash10-000x-3159000000-af2e9fcf16972a080c16Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-07dx-6014900000-a15808e923fac461291bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052b-0019400000-b68bd509e3cb87e17b70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1039000000-7ce4f783f36f7b9b084aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2193000000-7365c08f214addefd4d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-5005900000-2088e34c0a4a6a01ffcbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9005200000-a9d06f9e7f2d3992b3b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9002000000-16111b828c744dfe0370Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB017106
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751014
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.