Showing Compound Card for Vitexin-4'-o-rhamnoglucoside  (CDB000344)

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Record Information
Version1.0
Created at2020-03-19 00:32:02 UTC
Updated at2020-11-18 16:35:05 UTC
CannabisDB IDCDB000344
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameVitexin-4'-o-rhamnoglucoside 
Descriptionvitexin-o-rhamnoglucoside belongs to the class of organic compounds known as flavonoid c-glycosides. vitexin-o-rhamnoglucoside is a derivative of Vitexin. Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus (chaste tree or chasteberry), in the Phyllostachys nigra bamboo leaves, in the pearl millet (Pennisetum millet), and in Hawthorn. vitexin-4'-o-rhamnoglucoside is one of the flavonoids that have been identified in the cannabis plant. In vitexin-o-glucoside, with rhamnose and glucose either on 4 position of flavonoid or on the sugar moiety. If the Glucose attach on the sugar moiety, there are 5 possible isomer for that.(PMID: 6991645 )
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC33H40O19
Average Molecular Weight740.66
Monoisotopic Molecular Weight740.2164
IUPAC Name5,7-dihydroxy-8-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(4-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one
Traditional Name5,7-dihydroxy-8-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(4-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)chromen-4-one
CAS Registry NumberNot Available
SMILES
C[C@H]1O[C@@H](OC[C@@H]2O[C@H](OC3=CC=C(C=C3)C3=CC(=O)C4=C(O)C=C(O)C([C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)=C4O3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C33H40O19/c1-10-21(38)24(41)28(45)32(48-10)47-9-18-23(40)26(43)29(46)33(52-18)49-12-4-2-11(3-5-12)16-7-15(37)19-13(35)6-14(36)20(30(19)50-16)31-27(44)25(42)22(39)17(8-34)51-31/h2-7,10,17-18,21-29,31-36,38-46H,8-9H2,1H3/t10-,17-,18+,21-,22-,23-,24+,25+,26+,27-,28-,29-,31-,32-,33+/m1/s1
InChI KeyMHROQFYVRYVXRY-MGTKCHPPSA-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-8-c-glycoside
  • Flavonoid c-glycoside
  • Hydroxyflavonoid
  • Flavone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Phenolic glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Chromone
  • C-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • 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
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-3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)6.17ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area315.21 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity169.05 m³·mol⁻¹ChemAxon
Polarizability70.57 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 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 ]