Record Information
Version1.0
Creation date2010-04-08 22:09:55 UTC
Update date2019-11-26 03:05:49 UTC
Primary IDFDB011955
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuercetin 3-arabinoside
DescriptionQuercetin 3-arabinoside belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. Quercetin 3-arabinoside has been detected, but not quantified in, several different foods, such as fennels (Foeniculum vulgare), sweet bays (Laurus nobilis), common hazelnuts (Corylus avellana), anises (Pimpinella anisum), and american cranberries (Vaccinium macrocarpon). This could make quercetin 3-arabinoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Quercetin 3-arabinoside.
CAS Number22255-13-6
Structure
Thumb
Synonyms
SynonymSource
GuaiaverinHMDB
GuaijaverinHMDB
GuajavarinHMDB, MeSH
Quercetin 3-L-arabinosideHMDB
Quercetin 3-O-alpha-L-arabinopyranosideHMDB
Quercetin 3-O-alpha-L-arabinosideHMDB, MeSH
Quercetin 3-O-arabinosideHMDB
Foeniculinmanual
Quercetin 3-arabinosidemanual
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
Polarizability41.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H18O11
IUPAC name3-{[(2R,3R,4R,5S)-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/t13-,15-,17+,20+/m0/s1
InChI KeyBDCDNTVZSILEOY-BQCJVYABSA-N
Isomeric SMILESOC[C@@H]1O[C@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O
Average Molecular Weight434.3503
Monoisotopic Molecular Weight434.084911418
Classification
Description Belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentCurcuminoids
Alternative Parents
Substituents
  • Desmethoxycurcumin
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Phenol
  • 1,3-diketone
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Monocyclic benzene moiety
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Enone
  • Ketone
  • Ether
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

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 239° (hydrate)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data360 (e 24000) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSQuercetin 3-arabinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-074l-9002200000-2d25b1439162975be189Spectrum
Predicted GC-MSQuercetin 3-arabinoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-6900016000-052fe746be5b26272330Spectrum
Predicted GC-MSQuercetin 3-arabinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
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, Negativesplash10-001i-0000900000-5783c018f9dec347d81fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-0300900000-54efe938cd8127c33b3bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-1910200000-7f4dea7cc660d252c92fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-1453f61e7eeaeb92b36bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-a73a1bd1968f25a6dee4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-1911300000-24dd47b5a2f4224e1602Spectrum
NMRNot Available
ChemSpider ID8427825
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID10252339
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33795
CRC / DFC (Dictionary of Food Compounds) IDHBR39-C:HCB47-I
EAFUS IDNot Available
Dr. Duke IDFOENICULIN|GUAIJAVERIN|GUAIJAVARIN|QUERCETIN-3-ARABINOSIDE|QUERCETIN-3-L-ARABINOSIDE
BIGG IDNot Available
KNApSAcK IDC00005368
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
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— 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.