Showing Compound Card for 10-Oxo-delta-6a-tetrahydrocannabinol (CDB000037)

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Record Information
Version1.0
Created at2020-03-19 00:37:16 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000037
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name10-Oxo-delta-6a-tetrahydrocannabinol
Description10-Oxo-delta-6a-tetrahydrocannabinol (OTHC) 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. 10-Oxo-delta-6a-tetrahydrocannabinol is the oxidized derivative of delta-6a-tetrahydrocannabinol, carrying a ketone group at position 10. Very little information regarding its biological activities is available in the scientific literature. 10-Oxo-delta-6a-tetrahydrocannabinol is one of more than 120 cannabinoid compounds that are known to occur in cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC21H28O3
Average Molecular Weight328.45
Monoisotopic Molecular Weight328.2038
IUPAC Name(9S)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,7H,8H,9H,10H-cyclohexa[c]chromen-10-one
Traditional Name(9S)-1-hydroxy-6,6,9-trimethyl-3-pentyl-7H,8H,9H-cyclohexa[c]chromen-10-one
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC2=C(C(O)=C1)C1=C(CC[C@H](C)C1=O)C(C)(C)O2
InChI Identifier
InChI=1S/C21H28O3/c1-5-6-7-8-14-11-16(22)19-17(12-14)24-21(3,4)15-10-9-13(2)20(23)18(15)19/h11-13,22H,5-10H2,1-4H3/t13-/m0/s1
InChI KeyUEFGHYCIOXYTOG-ZDUSSCGKSA-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
  • Cyclohexenone
  • Alkyl aryl ether
  • Benzenoid
  • Ketone
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
logP5.55ALOGPS
logP5.71ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)8.96ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity97.11 m³·mol⁻¹ChemAxon
Polarizability38.76 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS10-Oxo-delta-6a-tetrahydrocannabinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS10-Oxo-delta-6a-tetrahydrocannabinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS10-Oxo-delta-6a-tetrahydrocannabinol, 2 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 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. Fuke G, Nornberg JL: Systematic evaluation on the effectiveness of conjugated linoleic acid in human health. Crit Rev Food Sci Nutr. 2017 Jan 2;57(1):1-7. doi: 10.1080/10408398.2012.716800. [PubMed:27636835 ]
  3. Cunnane SC, Anderson MJ: Pure linoleate deficiency in the rat: influence on growth, accumulation of n-6 polyunsaturates, and [1-14C]linoleate oxidation. J Lipid Res. 1997 Apr;38(4):805-12. [PubMed:9144095 ]
  4. Ruthig DJ, Meckling-Gill KA: Both (n-3) and (n-6) fatty acids stimulate wound healing in the rat intestinal epithelial cell line, IEC-6. J Nutr. 1999 Oct;129(10):1791-8. doi: 10.1093/jn/129.10.1791. [PubMed:10498749 ]
  5. Letawe C, Boone M, Pierard GE: Digital image analysis of the effect of topically applied linoleic acid on acne microcomedones. Clin Exp Dermatol. 1998 Mar;23(2):56-8. doi: 10.1046/j.1365-2230.1998.00315.x. [PubMed:9692305 ]
  6. Ando H, Ryu A, Hashimoto A, Oka M, Ichihashi M: Linoleic acid and alpha-linolenic acid lightens ultraviolet-induced hyperpigmentation of the skin. Arch Dermatol Res. 1998 Jul;290(7):375-81. doi: 10.1007/s004030050320. [PubMed:9749992 ]