Showing Compound Card for Ethoxy-cannabitriolvarin (CDB000439)

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Record Information
Version1.0
Created at2020-03-19 00:37:00 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000439
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameEthoxy-cannabitriolvarin
DescriptionEthoxy-cannabitriolvarin (CBTVE) is an ethoxylated derivative of cannabivarin (CBV). Unlike the methylated derivatives, which are naturally produced by the action of the SAM enzyme (PMID: 16766004 ), ethoxylated metabolites are very rarely found as plant natural products and are instead often found as artifacts produced during extraction procedures employing ethanol as the extraction solvent. CBTVE was isolated from a 140-year-old Cannabis sativa extract and reported in 1985 (PMID: 6991645 ). Regardless, ethoxy-cannabitriolvarin is one of more than 120 cannabinoid compounds reported to have been isolated from in Cannabis sativa (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC21H30O4
Average Molecular Weight346.47
Monoisotopic Molecular Weight346.2144
IUPAC Name(9S)-10-ethoxy-6,6,9-trimethyl-3-propyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,9-diol
Traditional Name(9S)-10-ethoxy-6,6,9-trimethyl-3-propyl-7H,8H,10H-cyclohexa[c]chromene-1,9-diol
CAS Registry NumberNot Available
SMILES
CCCC1=CC2=C(C(O)=C1)C1=C(CC[C@](C)(O)C1OCC)C(C)(C)O2
InChI Identifier
InChI=1S/C21H30O4/c1-6-8-13-11-15(22)18-16(12-13)25-20(3,4)14-9-10-21(5,23)19(17(14)18)24-7-2/h11-12,19,22-23H,6-10H2,1-5H3/t19-,21-/m0/s1
InChI KeyRFAYJRLIEJZHOI-FPOVZHCZSA-N
Chemical Taxonomy
ClassificationNot classified
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
logP3.86ALOGPS
logP3.92ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.24ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.65 m³·mol⁻¹ChemAxon
Polarizability39.86 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSEthoxy-cannabitriolvarin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEthoxy-cannabitriolvarin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEthoxy-cannabitriolvarin, 2 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 ]
  2. Roje S: S-Adenosyl-L-methionine: beyond the universal methyl group donor. Phytochemistry. 2006 Aug;67(15):1686-98. doi: 10.1016/j.phytochem.2006.04.019. [PubMed:16766004 ]