Record Information
Version1.0
Creation date2010-04-08 22:05:32 UTC
Update date2020-02-24 19:10:39 UTC
Primary IDFDB002820
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAvicularin
DescriptionAvicularin 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. Avicularin is an extremely weak basic (essentially neutral) compound (based on its pKa). Avicularin is found, on average, in the highest concentration within a few different foods, such as highbush blueberries, american cranberries, and lingonberries and in a lower concentration in apples, beers, and tea. Avicularin has also been detected, but not quantified in, several different foods, such as cocoa powders, guava, nuts, fruits, and pears. This could make avicularin a potential biomarker for the consumption of these foods.
CAS Number572-30-5
Structure
Thumb
Synonyms
SynonymSource
3-(a-L-Arabinofuranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one, 9ciHMDB
AvicularineHMDB
AvicularosideHMDB
FenicularinHMDB
Quercetin 3-a-L-arabofuranosideHMDB
Quercetin 3-alpha-L-arabinofuranosideHMDB
3-(a-L-Arabinofuranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility1.15 g/LALOGPS
logP0.76ALOGPS
logP0.49ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.31 m³·mol⁻¹ChemAxon
Polarizability40.37 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H18O11
IUPAC name3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2
InChI KeyBDCDNTVZSILEOY-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)C(O)C1O
Average Molecular Weight434.3503
Monoisotopic Molecular Weight434.084911418
Classification
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
  • Flavonoid-3-o-glycoside
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Pentose monosaccharide
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous acid
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Primary alcohol
  • 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 55.30%; H 4.18%; O 40.52%DFC
Melting PointMp 217° (anhyd. 222°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -241 (c, 0.138 in MeOH) -> -116 (24 hr)DFC
Spectroscopic UV Data360 (e 17400) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-074l-9002200000-165c1bc22134fd2b13d3Spectrum
Predicted GC-MSAvicularin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-074l-9002200000-165c1bc22134fd2b13d3Spectrum
Predicted GC-MSAvicularin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-6900016000-052fe746be5b26272330Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0179000000-5a91dfb63e4e3fdb59e8Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0009000000-bc5743bd40f3c7a2a0d5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-1239700000-28b26f9b0787af6359a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0269100000-7a94db25e6a9fec0926fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-3972000000-fc79be30bd59abcaa268Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-1115900000-e00178a2826bcd705265Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0649200000-08c4ad36ee9b747c1603Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgr-2952000000-5bfe8c304eb8f6a07051Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-1453f61e7eeaeb92b36bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-b96d174742d0ab482807Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-1910400000-98cf5ef937c3621d177cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-5783c018f9dec347d81fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0401900000-6d6d89904d44ae2a2c95Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f80-1911100000-ba0b08fba31dc160222bSpectrum
NMR
TypeDescriptionView
ChemSpider ID15727203
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID12308704
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID298
DrugBank IDNot Available
HMDB IDHMDB30860
CRC / DFC (Dictionary of Food Compounds) IDCNT75-X:CNT75-X
EAFUS IDNot Available
Dr. Duke IDAVICULARIN
BIGG IDNot Available
KNApSAcK IDC00005367
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
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
antibiotic22582 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
cyclooxygenase activatorDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
tissue thromboplastin inhibitor50427 A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.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.