Showing Compound Card for Cannabiripsol (CDB000447)

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Record Information
Version1.0
Created at2020-03-19 00:37:27 UTC
Updated at2020-11-18 16:35:10 UTC
CannabisDB IDCDB000447
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabiripsol
DescriptionCannabiripsol 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. Cannabiripsol is a cannabinoid, first isolated from a South African Cannabis variant and its structure was determined by spectrometric analysis and synthesis. Cannabirispsol corresponds to a dehydro derivative of cannabitriol (PMID: 499397 ). No further information regarding its biological activity has been published. It is one of the cannabinoid compounds identified in Cannabis sativa plants (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Cannabiripsol, (6ar-(6aalpha,9alpha,10beta,10abeta))-isomerMeSH
(6AR,9S,10S,10ar)-9,10-dihydroxyhexahydrocannabinolMeSH
Cannabiripsol, (6ar-(6aalpha,9alpha,10alpha,10abeta))-isomerMeSH
Chemical FormulaC21H32O4
Average Molecular Weight348.48
Monoisotopic Molecular Weight348.2301
IUPAC Name(6aR,9S,10S,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromene-1,9,10-triol
Traditional Name(6aR,9S,10S,10aR)-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10H,10aH-benzo[c]isochromene-1,9,10-triol
CAS Registry Number72236-32-9
SMILES
CCCCCC1=CC(O)=C2[C@@H]3[C@H](O)[C@@](C)(O)CC[C@H]3C(C)(C)OC2=C1
InChI Identifier
InChI=1S/C21H32O4/c1-5-6-7-8-13-11-15(22)18-16(12-13)25-20(2,3)14-9-10-21(4,24)19(23)17(14)18/h11-12,14,17,19,22-24H,5-10H2,1-4H3/t14-,17-,19+,21+/m1/s1
InChI KeyTZGCTXUTNDNTTE-DYZHCLJRSA-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
  • Cyclic alcohol
  • Tertiary alcohol
  • 1,2-diol
  • Secondary alcohol
  • Polyol
  • Ether
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen 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
logP4.11ALOGPS
logP3.96ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.9ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity98.93 m³·mol⁻¹ChemAxon
Polarizability40.93 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabiripsol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabiripsol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabiripsol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabiripsol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabiripsol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabiripsol, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabiripsol, 3 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 Compound192007
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Boeren EG, Elsohly MA, Turner CE: Cannabiripsol: a novel Cannabis constituent. Experientia. 1979 Oct 15;35(10):1278-9. doi: 10.1007/BF01963954. [PubMed:499397 ]
  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 ]