Showing Compound Card for 6a,7,10a-Trihydroxy-delta-9-tetrahydrocannabinol (CDB000039)

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Record Information
Version1.0
Created at2020-03-19 00:37:29 UTC
Updated at2020-12-07 19:07:26 UTC
CannabisDB IDCDB000039
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name6a,7,10a-Trihydroxy-delta-9-tetrahydrocannabinol
Description6a,7,10a trihydroxy-delta-9-tetrahydrocannabinol, also known as triOH-THC, 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. It is a trihydroxylated derivative of THC and one of the more than 120 cannabinoids that are known to occur in cannabis plants (PMID: 6991645 ). THC is the principal psychoactive constituent of cannabis. The actions of THC and THC derivatives result from their partial agonist activity on the cannabinoid receptor CB1, located mainly in the central nervous system, and the CB2 receptor, mainly expressed in cells of the immune system. 6a,7,10a-Trihydroxy-delta-9-tetrahydrocannabinnol was first isolated and identified as a cannabis constituent in 1979 from a hexane extract of small leaves, stems, and flowering tops of Mexican marijuana produced in Mississippi. The hexane soluble fractions were partitioned with KOH, and the aqueous layer was neutralized and extracted with petroleum ether and purified by column chromatography (PMID: 6991645 ). 6a,7,10a trihydroxy-delta-9-tetrahydrocannabinol is also found in cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC21H30O5
Average Molecular Weight362.47
Monoisotopic Molecular Weight362.2093
IUPAC Name(6aR,7R,10aS)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-1,6a,7,10a-tetrol
Traditional Name(6aR,7R,10aS)-6,6,9-trimethyl-3-pentyl-7H,8H-benzo[c]isochromene-1,6a,7,10a-tetrol
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC(O)=C2C(OC(C)(C)[C@@]3(O)[C@H](O)CC(C)=C[C@]23O)=C1
InChI Identifier
InChI=1S/C21H30O5/c1-5-6-7-8-14-10-15(22)18-16(11-14)26-19(3,4)21(25)17(23)9-13(2)12-20(18,21)24/h10-12,17,22-25H,5-9H2,1-4H3/t17-,20+,21+/m1/s1
InChI KeyANVPZESCUZNHQB-QMMLZNLJSA-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
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Secondary alcohol
  • Oxacycle
  • Polyol
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.56ALOGPS
logP3.1ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)9.83ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity100.61 m³·mol⁻¹ChemAxon
Polarizability41.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Receptors
Protein NameGene NameLocusUniprot IDDetails
Cannabinoid receptor 1CNR16q14-q15P21554 details
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 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. Kromhout D, Menotti A, Bloemberg B, Aravanis C, Blackburn H, Buzina R, Dontas AS, Fidanza F, Giampaoli S, Jansen A, et al.: Dietary saturated and trans fatty acids and cholesterol and 25-year mortality from coronary heart disease: the Seven Countries Study. Prev Med. 1995 May;24(3):308-15. doi: 10.1006/pmed.1995.1049. [PubMed:7644455 ]