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Showing Compound Quercetin 3-O-caffeyl-glucoside (FDB004800)

Record Information
Version1.0
Creation date2010-04-08 22:06:24 UTC
Update date2019-11-26 03:00:14 UTC
Primary IDFDB004800
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuercetin 3-O-caffeyl-glucoside
DescriptionQuercetin 3-o-caffeyl-glucoside is a member of the class of compounds known as flavonoid 3-o-p-coumaroyl glycosides. Flavonoid 3-o-p-coumaroyl glycosides are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Quercetin 3-o-caffeyl-glucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Quercetin 3-o-caffeyl-glucoside can be found in caraway, which makes quercetin 3-o-caffeyl-glucoside a potential biomarker for the consumption of this food product.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP2.58ALOGPS
logP2.28ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area253.13 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity152.8 m³·mol⁻¹ChemAxon
Polarizability60.52 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H26O15
IUPAC name[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
InChI IdentifierInChI=1S/C30H26O15/c31-14-9-19(36)23-20(10-14)43-28(13-3-5-16(33)18(35)8-13)29(25(23)39)45-30-27(41)26(40)24(38)21(44-30)11-42-22(37)6-2-12-1-4-15(32)17(34)7-12/h1-10,21,24,26-27,30-36,38,40-41H,11H2/b6-2+/t21-,24-,26+,27-,30+/m1/s1
InChI KeyIHBVMUCQCZEAPW-PFNFWJRHSA-N
Isomeric SMILESO[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C(O)=C2)O[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H]1O
Average Molecular Weight626.5184
Monoisotopic Molecular Weight626.127170162
Classification
Description Belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 3-O-p-coumaroyl glycosides
Alternative Parents
Substituents
  • Flavonoid 3-o-6-p-coumaroyl-glycoside
  • Flavonoid-3-o-glycoside
  • Flavone
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Chromone
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Fatty acid ester
  • Pyranone
  • Benzenoid
  • Oxane
  • Monocyclic benzene moiety
  • Monosaccharide
  • Fatty acyl
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0439306000-90973b8d6bdd805dcfa12016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0449100000-9f3be547ab53ccc3a99c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-0955000000-7e6070662792b7c49e262016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-0913103000-a4ca182e0b8811dbf5132016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w4i-0915000000-0af4ba3ead60739be8512016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w4i-0932000000-66df4e86c47d655cd3062016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000009000-3d1866ecbed6279163d42021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000009000-b9ee3f8c91ad2c6226662021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-1900113000-b8bbfca7a198de82b2da2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000009000-1b95243c30c5ad484c4b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0400019000-4a2bf3153006dda966442021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fc0-1910121000-31a2c4f64333a097fad42021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDQUERCETIN-3-O-CAFFEYL-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDNot Available
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
CarawayExpected but not quantifiedNot AvailableDUKE
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
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).