Showing Compound Card for acetylcannabispirol (CDB000321)

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Record Information
Version1.0
Created at2020-03-19 00:30:48 UTC
Updated at2020-11-18 16:35:04 UTC
CannabisDB IDCDB000321
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nameacetylcannabispirol
DescriptionAcetylcannabispirol is an acetylated derivative of cannabispiranol, which is derived from cannabispirone and cannabispirenone. It belongs to the class of organic compounds known as indan-1-spirocyclohexanes. These are organic aromatic compounds containing a cyclohexane moiety linked to the 1-position of an indane moiety in a spiro configuration. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. Acetylcannabispirol is also classified as a spiroindane compound. Spiroindane compounds were first isolated and identified as cannabis constituents in 1976. Spiroindane compounds are indane compounds that include two rings which share a single atom (usually a carbon). The simplest example of this type of compound is Spiro[2.2]pentane. Acetylcannabispirol is neutral, hydrophobic molecule that is insoluble in water. Acetylcannabispirol is one of several spiroindane, noncannabinoid compounds that are known in cannabis plants (PMID: 6991645 ). It was first isolated from the Japanese Kumamoto cannabis strain (DOI:10.1248/cpb.26.3641) and the β form was later identified in a Mexican variant of the cannabis plant (PMID: 18774146 ). The biogenetic relationship of spiro-compounds with cannabinoid acids was proposed (DOI:10.1248/cpb.26.3641).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1S,4R)-7'-Hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-yl acetic acidGenerator
Chemical FormulaC17H22O4
Average Molecular Weight290.36
Monoisotopic Molecular Weight290.1518
IUPAC Name(1s,4r)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-yl acetate
Traditional Name(1s,4r)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-yl acetate
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C(O)=C1)[C@]1(CC2)CC[C@@H](CC1)OC(C)=O
InChI Identifier
InChI=1S/C17H22O4/c1-11(18)21-13-4-7-17(8-5-13)6-3-12-9-14(20-2)10-15(19)16(12)17/h9-10,13,19H,3-8H2,1-2H3/t13-,17+
InChI KeyMNFMEFPMUGWNCI-XFHMXUHZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indan-1-spirocyclohexanes. These are organic aromatic compounds containing a cyclohexane moiety linked to the 1-position of an indane moiety in a spiro configuration.
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndanes
Sub ClassIndan-1-spirocyclohexanes
Direct ParentIndan-1-spirocyclohexanes
Alternative Parents
Substituents
  • Indan-1-spirocyclohexane
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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
logP3.28ALOGPS
logP3.03ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)10.11ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.23 m³·mol⁻¹ChemAxon
Polarizability31.83 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-MSacetylcannabispirol, 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
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. Radwan MM, Elsohly MA, Slade D, Ahmed SA, Wilson L, El-Alfy AT, Khan IA, Ross SA: Non-cannabinoid constituents from a high potency Cannabis sativa variety. Phytochemistry. 2008 Oct;69(14):2627-33. doi: 10.1016/j.phytochem.2008.07.010. Epub 2008 Sep 4. [PubMed:18774146 ]