Showing Compound Card for 2-Oxo-Delta3(4)-tetrahydrocannabinol (CDB000040)

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Record Information
Version1.0
Created at2020-04-27 17:26:22 UTC
Updated at2021-01-06 19:07:04 UTC
CannabisDB IDCDB000040
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Oxo-Delta3(4)-tetrahydrocannabinol
Description2-Oxo-Delta3(4)-tetrahydrocannabinol 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. 2-Oxo-Delta3(4)-tetrahydrocannabinol is one of cannabinoid compounds found in cannabis smoke. 2-Oxo-Delta3(4)-tetrahydrocannabinol is formed during the combustion of cannabis. 2-Oxo-Delta3(4)-tetrahydrocannabinol is an oxidative product of tetrahydrocannabinol. THC is the principal psychoactive constituent of cannabis. 2-Oxo-Delta3(4)-tetrahydrocannabinol is a secondary metabolite of cannabis. It is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC21H30O3
Average Molecular Weight330.47
Monoisotopic Molecular Weight330.2195
IUPAC Name1-hydroxy-6,6,9-trimethyl-3-pentyl-2H,3H,6H,7H,8H,9H,10H-cyclohexa[c]chromen-2-one
Traditional Name1-hydroxy-6,6,9-trimethyl-3-pentyl-3H,7H,8H,9H,10H-cyclohexa[c]chromen-2-one
CAS Registry NumberNot Available
SMILES
CCCCCC1C=C2OC(C)(C)C3=C(CC(C)CC3)C2=C(O)C1=O
InChI Identifier
InChI=1S/C21H30O3/c1-5-6-7-8-14-12-17-18(20(23)19(14)22)15-11-13(2)9-10-16(15)21(3,4)24-17/h12-14,23H,5-11H2,1-4H3
InChI KeyYCCKVKSVVJKWJF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassNot Available
Direct ParentPyrans
Alternative Parents
Substituents
  • Pyran
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Enol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.82ALOGPS
logP4.27ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)7.51ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.73 m³·mol⁻¹ChemAxon
Polarizability38.9 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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. Douros JD, Frankenfeld JW: Effects of Culture Conditions on Production of trans-Cinnamic Acid from Alkylbenzenes by Soil Microorganisms. Appl Microbiol. 1968 Feb;16(2):320-5. [PubMed:16349793 ]
  2. Vogt T: Phenylpropanoid biosynthesis. Mol Plant. 2010 Jan;3(1):2-20. doi: 10.1093/mp/ssp106. Epub 2009 Dec 24. [PubMed:20035037 ]