Read more...Show more...Show more...Show more...
Record Information
Version1.0
Created at2020-03-19 00:35:40 UTC
Updated at2022-12-13 21:44:20 UTC
CannabisDB IDCDB000001
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDelta-9-tetrahydrocannabinol
Description
Structure
Thumb
Synonyms
Chemical FormulaC21H30O2
Average Molecular Weight314.46
Monoisotopic Molecular Weight314.2246
IUPAC Name(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
Traditional NameTHC
CAS Registry Number1972-08-3
SMILES
CCCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1
InChI Identifier
InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
InChI KeyCYQFCXCEBYINGO-IAGOWNOFSA-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
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point200 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0026 g/LNot Available
logP5.648Not Available
Predicted Properties
PropertyValueSource
logP7.29ALOGPS
logP5.94ChemAxon
logS-5.1ALOGPS
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 Count4ChemAxon
Refractivity96.73 m³·mol⁻¹ChemAxon
Polarizability38.96 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-01pp-4792000000-06532e533cb7794b7c372014-09-20View Spectrum
Predicted GC-MSDelta-9-tetrahydrocannabinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0597-4090000000-670e40c1592b93325e44Spectrum
Predicted GC-MSDelta-9-tetrahydrocannabinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-6009000000-735bce5abc1be2637810Spectrum
Predicted GC-MSDelta-9-tetrahydrocannabinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDelta-9-tetrahydrocannabinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Multidrug resistance protein 1ABCB17q21.12P08183 details
ATP-binding cassette sub-family G member 2ABCG24q22Q9UNQ0 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Cytochrome P450 3A4CYP3A47q21.1P08684 details
Cytochrome P450 2C9CYP2C910q24P11712 details
Cytochrome P450 2C19CYP2C1910q24P33261 details
Cytochrome P450 1A1CYP1A115q24.1P04798 details
Cytochrome P450 2A6CYP2A619q13.2P11509 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Cannabinoid receptor 1CNR16q14-q15P21554 details
Cannabinoid receptor 2CNR21p36.11P34972 details
Transcriptional FactorsNot Available
Concentrations Data
HMDB IDHMDB0014613
DrugBank IDDB00470
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031310
KNApSAcK IDC00002675
Chemspider ID15266
KEGG Compound IDC06972
BioCyc IDCPD-7172
BiGG IDNot Available
Wikipedia LinkTetrahydrocannabinol
METLIN IDNot Available
PubChem Compound16078
PDB IDNot Available
ChEBI ID66964
References
General References
  1. Aizpurua-Olaizola O, Soydaner U, Ozturk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A: Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. J Nat Prod. 2016 Feb 26;79(2):324-31. doi: 10.1021/acs.jnatprod.5b00949. Epub 2016 Feb 2. [PubMed:26836472 ]
  2. Koh WS, Crawford RB, Kaminski NE: Inhibition of protein kinase A and cyclic AMP response element (CRE)-specific transcription factor binding by delta9-tetrahydrocannabinol (delta9-THC): a putative mechanism of cannabinoid-induced immune modulation. Biochem Pharmacol. 1997 May 15;53(10):1477-84. doi: 10.1016/s0006-2952(97)82441-0. [PubMed:9260875 ]
  3. Little PJ, Martin BR: The effects of delta 9-tetrahydrocannabinol and other cannabinoids on cAMP accumulation in synaptosomes. Life Sci. 1991;48(12):1133-41. doi: 10.1016/0024-3205(91)90450-p. [PubMed:1848340 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Enzymes

General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
General function:
Involved in ATP binding
Specific function:
Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular weight:
72313.5

Only showing the first 10 proteins. There are 12 proteins in total.