Showing Compound Card for 10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol (CDB000034)

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Record Information
Version1.0
Created at2020-03-19 00:36:52 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000034
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol
Description10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. 10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol is one of more than 120 cannabinoid compounds that are known in cannabis plants (PMID: 6991645 ). 10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol is an ethoxylated derivative of cannabitriol (CBT). Unlike the methylated derivatives, which are naturally produced by the action of the SAM enzyme (PMID: 16766004 ), ethoxylated metabolites are very rarely found as plant natural products and are instead often found as artifacts produced during extraction procedures employing ethanol as the extraction solvent. The isolation of 10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol from Cannabis sativa extracts was reported in 1977, together with cannabitriol (PMID: 895385 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(9S)-3-Pentyl-6,6,9-trimethyl-10a-ethoxy-7,8,9,10-tetrahydro-6H-dibenzo[b,D]pyran-1,9a-diolGenerator
(9S)-3-Pentyl-6,6,9-trimethyl-10α-ethoxy-7,8,9,10-tetrahydro-6H-dibenzo[b,D]pyran-1,9α-diolGenerator
Chemical FormulaC23H34O4
Average Molecular Weight374.52
Monoisotopic Molecular Weight374.2457
IUPAC Name(9S,10R)-10-ethoxy-6,6,9-trimethyl-3-pentyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,9-diol
Traditional Name(9S,10R)-10-ethoxy-6,6,9-trimethyl-3-pentyl-7H,8H,10H-cyclohexa[c]chromene-1,9-diol
CAS Registry NumberNot Available
SMILES
CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2[C@@H](OCC)[C@@](C)(O)CC3)=C1
InChI Identifier
InChI=1S/C23H34O4/c1-6-8-9-10-15-13-17(24)20-18(14-15)27-22(3,4)16-11-12-23(5,25)21(19(16)20)26-7-2/h13-14,21,24-25H,6-12H2,1-5H3/t21-,23+/m1/s1
InChI KeyHRAUOPAWWNBNRN-GGAORHGYSA-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
  • Tertiary alcohol
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • 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
logP4.82ALOGPS
logP4.8ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.24ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity108.86 m³·mol⁻¹ChemAxon
Polarizability44.12 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS10-Ethoxy-9-hydroxy-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 Compound49871313
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. Roje S: S-Adenosyl-L-methionine: beyond the universal methyl group donor. Phytochemistry. 2006 Aug;67(15):1686-98. doi: 10.1016/j.phytochem.2006.04.019. [PubMed:16766004 ]
  3. Elsohly MA, El-Feraly FS, Turner CE: Isolation and characterization of (+)-cannabitriol and (-)-10-ethoxy-9-hydroxy-delta 6a[10a]-tetrahydrocannabinol: two new cannabinoids from Cannabis sativa L. extract. Lloydia. 1977 May-Jun;40(3):275-80. [PubMed:895385 ]
  4. Groce JW, Jones LA: Carbohydrate and cyclitol content of cannabis. J Agric Food Chem. 1973 Mar-Apr;21(2):211-4. doi: 10.1021/jf60186a003. [PubMed:4688907 ]