Showing Compound Card for Delta-9-tetrahydrocannabiorcol (CDB000416)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (1) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:35:54 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000416
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDelta-9-tetrahydrocannabiorcol
DescriptionDelta-9-Tetrahydrocannabiorcol, also known as THC-C1, 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. Delta-9-Tetrahydrocannabiorcol is a neutral compound . Delta-9-Tetrahydrocannabiorcol is one of more than 120 cannabinoid compounds that are known in cannabis plant (PMID: 6991645 ). It belongs to the delta-9-tetrahydrocannabinol class of cannabinoid compounds in the cannabis plant that has CH3 substituent positioning on C-3 (PMID: 6991645 ). A study has shown that delta-9-tetrahydrocannabiorcol acid binds cannabinoid type one (CB1) and type 2 (CB2) receptors and displayed the highest activity on transient receptor potential ankyrin 1 (TRPA1), a unique sensor of noxious stimuli and a potential drug target for analgesics, without affecting the cannabinoid receptors (PMID: 22109525 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC17H22O2
Average Molecular Weight258.36
Monoisotopic Molecular Weight258.162
IUPAC Name(6aR,10aR)-3,6,6,9-tetramethyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
Traditional Name(6aR,10aR)-3,6,6,9-tetramethyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
CAS Registry Number22972-65-2
SMILES
CC1=C[C@@H]2[C@@H](CC1)C(C)(C)OC1=CC(C)=CC(O)=C21
InChI Identifier
InChI=1S/C17H22O2/c1-10-5-6-13-12(7-10)16-14(18)8-11(2)9-15(16)19-17(13,3)4/h7-9,12-13,18H,5-6H2,1-4H3/t12-,13-/m1/s1
InChI KeyWIDIPARNVYRVNW-CHWSQXEVSA-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
logP4.87ALOGPS
logP4.17ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.37ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity78.33 m³·mol⁻¹ChemAxon
Polarizability30.41 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDelta-9-tetrahydrocannabiorcol, 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
Transporters
Protein NameGene NameLocusUniprot IDDetails
Transient receptor potential cation channel subfamily A member 1TRPA18q13O75762 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Cannabinoid receptor 1CNR16q14-q15P21554 details
Transient receptor potential cation channel subfamily A member 1TRPA18q13O75762 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 Compound22805649
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. Andersson DA, Gentry C, Alenmyr L, Killander D, Lewis SE, Andersson A, Bucher B, Galzi JL, Sterner O, Bevan S, Hogestatt ED, Zygmunt PM: TRPA1 mediates spinal antinociception induced by acetaminophen and the cannabinoid Delta(9)-tetrahydrocannabiorcol. Nat Commun. 2011 Nov 22;2:551. doi: 10.1038/ncomms1559. [PubMed:22109525 ]

Transporters

Enzyme Details
1. Transient receptor potential cation channel subfamily A member 1
General function:
Not Available
Specific function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function. Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes. Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)- tetrahydrocannabinol (THC), the psychoactive component of marijuana. Not involved in menthol sensation. May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular weight:
127485.8