Record Information
Version1.0
Created at2020-03-19 00:35:05 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000008
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabichromevarinic acid
DescriptionCannabichromevarinic acid (CBCVA), a biosynthetic derivative of cannabigerovarinic acid (CBGVA),  is a non-psychoactive component of cannabis. CBCVA is a C3 analogue of cannabichromenic acid. CBCVA is one of the more than 100 cannabinoids found in Cannabis sativa plants. As its precursor, cannabigerovarinic acid, CBCVA is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabichromenic acid is characterized by the presence of a chromene (1-benzopyran) moiety in the center of the structure. This chromene arrangement results from the cyclization of the isoprenoid sidechain onto the hydroxyl group in position four of cannabigerovarinic acid, yielding a pyrane type ring. Cannabichromevarinic acid is a molecule of mixed biosynthetic oDOI: rigin, in which its aromatic moiety (derived from divarinic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). As such, cannabichromevarinic acid can be considered a polyketide, a monoterpenoid and a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring.  CBCVA was one of four propyl cannabinoid acids isolated from Thai Cannabis, 'Meao Variant' in 1977 (DOI: 10.1248/cpb.25.2306).
Structure
Thumb
Synonyms
ValueSource
(2S)-5-Hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propyl-2H-chromene-6-carboxylateGenerator
Chemical FormulaC20H26O4
Average Molecular Weight330.42
Monoisotopic Molecular Weight330.1831
IUPAC Name(2S)-5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propyl-2H-chromene-6-carboxylic acid
Traditional Name(2S)-5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propylchromene-6-carboxylic acid
CAS Registry Number64898-02-8
SMILES
CCCC1=CC2=C(C=C[C@](C)(CCC=C(C)C)O2)C(O)=C1C(O)=O
InChI Identifier
InChI=1S/C20H26O4/c1-5-7-14-12-16-15(18(21)17(14)19(22)23)9-11-20(4,24-16)10-6-8-13(2)3/h8-9,11-12,21H,5-7,10H2,1-4H3,(H,22,23)/t20-/m0/s1
InChI KeyOIVPAQDCMDYIIL-FQEVSTJZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylic acid and derivatives
Alternative Parents
Substituents
  • 1-benzopyran
  • Salicylic acid or derivatives
  • Benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP5.06ALOGPS
logP6.02ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)2.87ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.66 m³·mol⁻¹ChemAxon
Polarizability37.1 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabichromevarinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabichromevarinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabichromevarinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableSpectrum
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 ReferencesNot Available