Showing Compound Card for Delta-9-tetrahydrocannabinol-C4 (CDB000019)

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Record Information
Version1.0
Created at2020-03-19 00:35:42 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000019
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDelta-9-tetrahydrocannabinol-C4
DescriptionDelta-9-Tetrahydrocannabinol-C4, also known as THC-C4, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. Delta-9-Tetrahydrocannabinol-C4, first identified from cannabis, were characterized by gas chromatography-mass spectrometry (GC-MS) of the ethyl acetate extract of ten police confiscated cannabis resins, tinctures and leaves in 1976 (PMID: 6715 ). It is one of more than 120 cannabinoid compounds identified in cannabis plant. It belongs to the delta-9-tetrahydrocannabinol class of cannabinoid compounds in the cannabis plant that has C4H9 substituent positioning on C-3 (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Butyl-δ(9)-tetrahydrocannabinolGenerator
Butyl-delta(9)-THCMeSH
Butyl-delta(9)-tetrahydrocannabinolMeSH
Chemical FormulaC20H28O2
Average Molecular Weight300.44
Monoisotopic Molecular Weight300.2089
IUPAC Name(6aR,10aR)-3-butyl-6,6,9-trimethyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
Traditional Name(6aR,10aR)-3-butyl-6,6,9-trimethyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
CAS Registry Number60008-00-6
SMILES
CCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1
InChI Identifier
InChI=1S/C20H28O2/c1-5-6-7-14-11-17(21)19-15-10-13(2)8-9-16(15)20(3,4)22-18(19)12-14/h10-12,15-16,21H,5-9H2,1-4H3/t15-,16-/m1/s1
InChI KeyQHCQSGYWGBDSIY-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
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • 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
logP6.69ALOGPS
logP5.5ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.34ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity92.13 m³·mol⁻¹ChemAxon
Polarizability36.71 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDelta-9-tetrahydrocannabinol-C4, 1 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
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4956237
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6453891
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Harvey DJ: Characterization of the butyl homologues of delta1-tetrahydrocannabinol, cannabinol and cannabidiol in samples of cannabis by combined gas chromatography and mass spectrometry. J Pharm Pharmacol. 1976 Apr;28(4):280-5. doi: 10.1111/j.2042-7158.1976.tb04153.x. [PubMed:6715 ]
  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 ]