Showing Compound Card for 2"-o-Glucopyranosylvitexin (CDB000791)

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Record Information
Version1.0
Created at2020-03-19 00:57:11 UTC
Updated at2020-12-07 19:07:46 UTC
CannabisDB IDCDB000791
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2"-o-Glucopyranosylvitexin
Description2"-O-Glucopyranosylvitexin, belongs to the class of organic compounds known as flavonoid 8-O-glycosides. Flavonoid 8-O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. 2"-O-Glucopyranosylvitexin is a glucopyranose derivative of the flavonoid known as vitexin. Vitexin is an apigenin flavone glucoside which is found in the passion flower, chaste tree or chasteberry, bamboo leaves, pearl millet and in Hawthorn. 2"-O-Glucopyranosylvitexin was first isolated and identified as a cannabis constituent in 1976 and the structure was described as 2"-O-Glucopyranosylvitexin in 1978 ( Ref:DOI ). Vitexin and its derivatives exhibit anti-inflammatory, anti-histamic, anti-cancer and antibradykinin activities among a broad range of other biological activities including antioxidant properties (PMID: 29407975 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC27H30O15
Average Molecular Weight594.52
Monoisotopic Molecular Weight594.1585
IUPAC Name8-[(2R,3S,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Name8-[(2R,3S,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@H](O[C@H]2[C@@H](O)[C@H](O)[C@H](CO)O[C@@H]2C2=C(O)C=C(O)C3=C2OC(=CC3=O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C27H30O15/c28-7-15-20(35)22(37)26(42-27-23(38)21(36)19(34)16(8-29)41-27)25(40-15)18-12(32)5-11(31)17-13(33)6-14(39-24(17)18)9-1-3-10(30)4-2-9/h1-6,15-16,19-23,25-32,34-38H,7-8H2/t15-,16+,19+,20+,21-,22-,23+,25+,26-,27+/m0/s1
InChI KeyFYTOTHFWELWOCG-FIPOCJBLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • Hydroxyflavonoid
  • Flavone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Phenolic glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Chromone
  • C-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Dialkyl ether
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • 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
logP-0.7ALOGPS
logP-1.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)6.17ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area256.29 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity138.45 m³·mol⁻¹ChemAxon
Polarizability55.8 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2"-o-Glucopyranosylvitexin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2"-o-Glucopyranosylvitexin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2"-o-Glucopyranosylvitexin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2"-o-Glucopyranosylvitexin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2"-o-Glucopyranosylvitexin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2"-o-Glucopyranosylvitexin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2"-o-Glucopyranosylvitexin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2"-o-Glucopyranosylvitexin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2"-o-Glucopyranosylvitexin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2"-o-Glucopyranosylvitexin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Ling T, Lang W, Feng X, Das S, Maier J, Jeffries C, Shelat A, Rivas F: Novel vitexin-inspired scaffold against leukemia. Eur J Med Chem. 2018 Feb 25;146:501-510. doi: 10.1016/j.ejmech.2018.01.004. Epub 2018 Jan 31. [PubMed:29407975 ]