Showing Compound Card for Isovitexin- 4'-o-glucoside (CDB000338)

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Record Information
Version1.0
Created at2020-03-19 00:31:43 UTC
Updated at2020-11-18 16:35:04 UTC
CannabisDB IDCDB000338
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameIsovitexin- 4'-o-glucoside
Descriptionisovitexin- o-glucoside belongs to the class of organic compounds known as flavonoid C-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. isovitexin-4'- o-glucoside was found in the cannabis plant. It is a derivative of isovitexin that the glucoside moiety positionong on C-4'. Isovitexin (or homovitexin, saponaretin) is a flavone. It can be found in the passion flower, Cannabis, and the açaí palm. In fact, isovitexin-o-glucoside is one of the flavonoid glycosides that were identified in the cannabis plant and the glucose moiety can be attached either to 4 position of the flavonoid or on the sugar moiety). If the Glucoside attach on the sugar moiety, there are 5 possible isomer for that.(PMID: 6991645 )
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC27H30O15
Average Molecular Weight594.52
Monoisotopic Molecular Weight594.1585
IUPAC Name5,7-dihydroxy-6-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one
Traditional Name5,7-dihydroxy-6-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OC2=CC=C(C=C2)C2=CC(=O)C3=C(O)C([C@H]4O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]4O)=C(O)C=C3O2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C27H30O15/c28-7-15-19(32)22(35)24(37)26(41-15)18-12(31)6-14-17(21(18)34)11(30)5-13(40-14)9-1-3-10(4-2-9)39-27-25(38)23(36)20(33)16(8-29)42-27/h1-6,15-16,19-20,22-29,31-38H,7-8H2/t15-,16+,19-,20+,22+,23-,24-,25+,26+,27+/m0/s1
InChI KeySFNFQCXADNWOCI-FWWRQVNSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid o-glycoside
  • Flavonoid-4p-o-glycoside
  • Flavonoid c-glycoside
  • Hydroxyflavonoid
  • Flavone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Phenolic glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • C-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • 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
Not Available
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-0.75ALOGPS
logP-2.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.14ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area256.29 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity138.18 m³·mol⁻¹ChemAxon
Polarizability58.45 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-MSIsovitexin- 4'-o-glucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsovitexin- 4'-o-glucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsovitexin- 4'-o-glucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsovitexin- 4'-o-glucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsovitexin- 4'-o-glucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsovitexin- 4'-o-glucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsovitexin- 4'-o-glucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsovitexin- 4'-o-glucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsovitexin- 4'-o-glucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsovitexin- 4'-o-glucoside, 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. 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 ]