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Showing Compound Avicularin (FDB002820)

Record Information
Version1.0
Creation date2010-04-08 22:05:32 UTC
Update date2025-11-18 22:40:56 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 found, on average, in the highest concentration within a few different foods, such as highbush blueberries (Vaccinium corymbosum), american cranberries (Vaccinium macrocarpon), and lingonberries (Vaccinium vitis-idaea) and in a lower concentration in grape wine, teas (Camellia sinensis), and beer. Avicularin has also been detected, but not quantified in, several different foods, such as allspices (Pimenta dioica), fennels (Foeniculum vulgare), guavas (Psidium guajava), cocoa powder, and pears (Pyrus communis). This could make avicularin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Avicularin.
CAS Number572-30-5
Structure
Thumb
MOLSDFPDBSMILESInChI
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
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
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
Predicted GC-MSAvicularin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAvicularin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0179000000-5a91dfb63e4e3fdb59e82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0009000000-bc5743bd40f3c7a2a0d52017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-1239700000-28b26f9b0787af6359a82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0269100000-7a94db25e6a9fec0926f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-3972000000-fc79be30bd59abcaa2682016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-1115900000-e00178a2826bcd7052652016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0649200000-08c4ad36ee9b747c16032016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgr-2952000000-5bfe8c304eb8f6a070512016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-1453f61e7eeaeb92b36b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-b96d174742d0ab4828072021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-1910400000-98cf5ef937c3621d177c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-5783c018f9dec347d81f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0401900000-6d6d89904d44ae2a2c952021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f80-1911100000-ba0b08fba31dc160222b2021-09-22View Spectrum
NMRNot Available
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 IDAvicularin
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 agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Antibiotic22582 An agent that inhibits the growth of or destroys microorganisms, particularly bacteria. Therapeutically, antibiotics are used to treat bacterial infections, such as pneumonia, tuberculosis, and skin infections, by targeting specific biochemical processes essential for microbial survival.DUKE
Cyclooxygenase activatorAn agent that stimulates cyclooxygenase, enhancing prostanoid formation, including prostaglandins. It has therapeutic applications in cardiovascular health and may be used to manage conditions like atherosclerosis and thrombosis, promoting blood flow and preventing clotting.DUKE
Diuretic35498 An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Tissue thromboplastin inhibitor50427 An agent that blocks tissue thromboplastin, reducing blood clot formation. It has therapeutic applications in preventing thrombosis and is commonly used in managing cardiovascular disorders, such as deep vein thrombosis and pulmonary embolism.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.