Showing Compound Card for Delta-9-tetrahydrocannabivarinic acid (CDB000020)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferences Show 1 proteinXML
Record Information
Version1.0
Created at2020-03-19 00:35:46 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000020
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDelta-9-tetrahydrocannabivarinic acid
DescriptionDelta-9-tetrahydrocannabivarinic acid, also known as, THCVA, belongs to the delta-9-tetrahydrocannabinol class of cannabinoid compounds in cannabis plant. Delta-9-tetrahydrocannabivarinic acid is one of more than 120 cannabinoid compounds that have been identified in the cannabis plant. Mass spectral evidence of THCVA presence in cannabis was reported in 1973 based on the evaluation of 51 samples from different geographical locations (PMID: 4752132 ). Its structure is like delta-9-THCV except for the carboxyl functional group positioning on C-2 in delta-9-THCVA. (PMID: 6991645 ). The proposed biosynthesis of THCVA was as following: divarinolic acid is formed by the condensation of three molecules of malonyl-CoA and one molecule of n-Butyl-CoA, which yields cannabigerovarinic acid (CBGVA) through geranyl diphosphate (GPP) synthase and is converted into THCVA (DOI: 10.1007/s11101-008-9094-4, DOI: 10.1016/S0031-9422(00)84939-0).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC20H26O4
Average Molecular Weight330.42
Monoisotopic Molecular Weight330.1831
IUPAC Name(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-propyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid
Traditional Name(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-propyl-6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid
CAS Registry Number39986-26-0
SMILES
CCCC1=C(C(O)=O)C(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1
InChI Identifier
InChI=1S/C20H26O4/c1-5-6-12-10-15-17(18(21)16(12)19(22)23)13-9-11(2)7-8-14(13)20(3,4)24-15/h9-10,13-14,21H,5-8H2,1-4H3,(H,22,23)/t13-,14-/m1/s1
InChI KeyIQSYWEWTWDEVNO-ZIAGYGMSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent2,2-dimethyl-1-benzopyrans
Alternative Parents
Substituents
  • 2,2-dimethyl-1-benzopyran
  • Hydroxybenzoic acid
  • Salicylic acid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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
logP4.34ALOGPS
logP5.36ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.79 m³·mol⁻¹ChemAxon
Polarizability37.6 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDelta-9-tetrahydrocannabivarinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelta-9-tetrahydrocannabivarinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelta-9-tetrahydrocannabivarinic acid, 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
Receptors
Protein NameGene NameLocusUniprot IDDetails
Cannabinoid receptor 2CNR21p36.11P34972 details
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 Compound59444416
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Hadley K, Fetterman PS: Constituents of Cannabis sativa L. VI. Propyl homologs in samples of known geographical origin. J Pharm Sci. 1973 Oct;62(10):1739-41. doi: 10.1002/jps.2600621045. [PubMed:4752132 ]
  2. 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 ]