Showing Compound Card for Delta-8-tetrahydrocannabinolic acid (CDB000023)

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Record Information
Version1.0
Created at2020-03-19 00:36:00 UTC
Updated at2023-06-26 21:34:43 UTC
CannabisDB IDCDB000023
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDelta-8-tetrahydrocannabinolic acid
DescriptionDelta-8-tetrahydrocannabinolic acid, also known as Delta-8-THCA, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. Detla-8-tetrahydrocannabinolic acid is one of more than 120 cannabinoid compounds that are known in cannabis plant. It is one of the only two delta-8-THC-type cannabinoids in cannabis, namely delta-8-THC and delta-8-THCA. Delta-8-THC and its acid precursor are considered as THC and THC acid artifacts, respectively. The 8,9 double-bond position is thermodynamically more stable than the 9,10 position. Delta-8-THC is approximately 20% less active than THC (PMID: 6991645 ). THC acid is produced via the following pathway: Geranyl pyrophosphate and olivetolic acid react, catalyzed by an enzyme Geranyl-pyrophosphate—olivetolic acid geranyltransferase to produce cannabigerolic acid which is then cyclized by the enzyme THC acid synthase to give THC acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC22H30O4
Average Molecular Weight358.48
Monoisotopic Molecular Weight358.2144
IUPAC Name(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,10H,10aH-benzo[c]isochromene-2-carboxylic acid
Traditional Name(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6aH,7H,10H,10aH-benzo[c]isochromene-2-carboxylic acid
CAS Registry Number23978-89-4
SMILES
CCCCCC1=CC2=C([C@@H]3CC(C)=CC[C@H]3C(C)(C)O2)C(O)=C1C(O)=O
InChI Identifier
InChI=1S/C22H30O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h9,12,15-16,23H,5-8,10-11H2,1-4H3,(H,24,25)/t15-,16-/m1/s1
InChI KeyYKKHSYLGQXKVMO-HZPDHXFCSA-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
logP5.42ALOGPS
logP6.25ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity103.99 m³·mol⁻¹ChemAxon
Polarizability41.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDelta-8-tetrahydrocannabinolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelta-8-tetrahydrocannabinolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelta-8-tetrahydrocannabinolic 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
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified209 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified205 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified121 mg/g dry wt
    • David S. Wishart,...
 details
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 Compound59444391
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 ]