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Showing Compound Quercetin 7-glucoside (FDB002523)

Record Information
Version1.0
Creation date2010-04-08 22:05:24 UTC
Update date2019-11-26 02:57:33 UTC
Primary IDFDB002523
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuercetin 7-glucoside
DescriptionQuercetin 7-glucoside, also known as quercimeritrin, is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Quercetin 7-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Quercetin 7-glucoside can be found in a number of food items such as roman camomile, okra, dandelion, and cottonseed, which makes quercetin 7-glucoside a potential biomarker for the consumption of these food products.
CAS Number491-50-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-3,5-dihydroxy-4H-1-benzopyran-4-oneChEBI
3,5-Dihydroxy-2-(3,4-dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-4H-1-benzopyran-4-oneChEBI
Quercetin 7-O-glucosideChEBI
QuercimeritrinChEBI
QuercimeritrosideChEBI
2-(3,4-Dihydroxyphenyl)-7-(b-D-glucopyranosyloxy)-3,5-dihydroxy-4H-1-benzopyran-4-oneGenerator
2-(3,4-Dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-3,5-dihydroxy-4H-1-benzopyran-4-oneGenerator
3,5-Dihydroxy-2-(3,4-dihydroxyphenyl)-7-(b-D-glucopyranosyloxy)-4H-1-benzopyran-4-oneGenerator
3,5-Dihydroxy-2-(3,4-dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-4H-1-benzopyran-4-oneGenerator
Quercetin 7-O-b-D-glucosideGenerator
Quercetin 7-O-β-D-glucosideGenerator
Quercetin 7-O-beta-D-glucosideKEGG
7-Glucosyl quercetinbiospider
7-O-b-D-Glucopyranosyloxy-3,3',4',5-tetrahydroxyflavonedb_source
Glucosyl-7-quercetinbiospider
Quercetin 7-β-D-glucopyranosidebiospider
Quercetin 7-β-D-glucosidebiospider
Quercetin 7-glucosidedb_source
Quercetin 7-monoglucosidebiospider
Quercetin 7-O-β-D-glucopyranosidebiospider
Predicted Properties
PropertyValueSource
Water Solubility1.61 g/LALOGPS
logP0.62ALOGPS
logP-0.11ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)7.98ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.01 m³·mol⁻¹ChemAxon
Polarizability43.89 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H20O12
IUPAC name2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
InChI IdentifierInChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)31-8-4-11(25)14-12(5-8)32-20(18(29)16(14)27)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1
InChI KeyBBFYUPYFXSSMNV-HMGRVEAOSA-N
Isomeric SMILESOC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight464.3763
Monoisotopic Molecular Weight464.095476104
Classification
Description Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • 3-hydroxyflavone
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Phenol
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.32%; H 4.34%; O 41.34%DFC
Melting PointMp 249-250°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data372 (e 21380) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0238900000-883c3bbdc311fa7ca6f42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0289100000-18024073da2fe00c127b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-3982000000-e481f4008f162cc01c3e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-1216900000-175a1bc230654e57381e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1329200000-fb2550dfb0fc37d49e532016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-5595000000-24c083c5d8a74099dc862016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0009400000-82ee0af7a45dc332bf032021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009100000-7cb9d26c1cc75ab3087e2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0009000000-83a0d85bdd6b793b4e432021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-5b89d1f188186f3081cb2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ik9-0005900000-e1e3f4f430433969300b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0009100000-1b81e54574c3c212f5362021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC12639
Pubchem Compound ID5282160
Pubchem Substance IDNot Available
ChEBI ID28529
Phenol-Explorer ID372
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCMG40-P:CMG40-P
EAFUS IDNot Available
Dr. Duke IDQUERCETIN-7-O-BETA-D-GLUCOSIDE|QUERCETIN-7-GLUCOSIDE|QUECIMERITRIN|QUERCIMERITRIN
BIGG IDNot Available
KNApSAcK IDC00005382
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 herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
Insectiphile24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.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.