Showing Compound Card for quercetin-o-glucoside (CDB000792)

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Record Information
Version1.0
Created at2020-03-19 00:57:13 UTC
Updated at2020-12-07 19:07:46 UTC
CannabisDB IDCDB000792
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namequercetin-o-glucoside
DescriptionQuercetin-O-glucoside is a general term to reference a group of secondary metabolites sharing quercetin as the flavonoid aglicone and that are glucosilated at any of the five hydroxyl groups in its structure. Quercetin-3-O-glucoside is one example of such a derivative of quercetin with a glucose moiety positioned on C-3 of the quercetin molecule (PMID: 17269003 ). Quercetin is the most abundant flavonoid in the human diet, but it is very often found as a polar, glycosylated derivative in nature, which makes it difficult to absorb in the human digestive tract. However, after ingestion most polyphenolic glycosides are hydrolyzed, releasing the polyphenolic aglycone (in this case quercetin) and allowing its quick absortion. Quercetin has shown significant pharmacological properties, mostly regarding its anti-oxidant capacity which impacts the effect of dietary quercetin preventing inflammation, cancer, tissue aging and neurodegenerative diseases (PMID: 28082789 ). Quercetin-3-O-glucoside is one of the flavonoid glycosides that have been found in cannabis plants (PMID: 6991645 ). Furthermore, cell suspension cultures of Cannabis sativa without endogenous quercetin, were shown to biotranform exogenously applied quercetin into glycosylated derivatives (PMID: 17269003 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC21H20O12
Average Molecular Weight464.38
Monoisotopic Molecular Weight464.0955
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17-,18+,21+/m1/s1
InChI KeyOVSQVDMCBVZWGM-FZEMLGNSSA-N
Chemical Taxonomy
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
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • 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 DescriptorsNot Available
Ontology
Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.47ALOGPS
logP-0.14ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.28 m³·mol⁻¹ChemAxon
Polarizability43.14 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound57497930
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Braemer R, Tsoutsias Y, Hurabielle M, Paris M: Biotransformations of Quercetin and Apigenin by a Cell Suspension Culture of Cannabis sativa. Planta Med. 1987 Apr;53(2):225-6. doi: 10.1055/s-2006-962682. [PubMed:17269003 ]
  2. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  3. Anand David AV, Arulmoli R, Parasuraman S: Overviews of Biological Importance of Quercetin: A Bioactive Flavonoid. Pharmacogn Rev. 2016 Jul-Dec;10(20):84-89. doi: 10.4103/0973-7847.194044. [PubMed:28082789 ]