Showing Compound Card for Anhydrocannabisativine (CDB000234)

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Record Information
Version1.0
Created at2020-03-19 00:25:59 UTC
Updated at2020-12-07 19:07:17 UTC
CannabisDB IDCDB000234
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAnhydrocannabisativine
DescriptionAnhydrocannabisativine belongs to the class of organic compounds known as macrolactams, it is an alkaloid isolated from Cannabis sativa L. roots and leafs and its structure was established by spectral analysis and semisynthesis (PMID: 619102 , PMID: 6991645 ). Anhydrocannabisativine is the dehydrated form of cannabisativine. The difference in their structures appears on the substituents on C2: anhydrocannabisativine has the alkyl-keto on C2 of the side chain (PMID: 619102 ). Although the biological activity of anhydrocannabisativine has yet to be investigated, it has been isolated from Cannabis root extracts which have been found to be useful in the treatment of inflammation, joint pain, gout, and other conditions (PMID: 29082318 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC21H37N3O2
Average Molecular Weight363.55
Monoisotopic Molecular Weight363.2886
IUPAC Name1-[(13R,16aR)-2-hydroxy-1H,4H,5H,6H,7H,8H,9H,10H,11H,13H,16H,16aH-pyrido[2,1-d]1,5,9-triazacyclotridecan-13-yl]heptan-2-one
Traditional Name1-[(13R,16aR)-2-hydroxy-1H,4H,5H,6H,7H,8H,9H,10H,11H,13H,16H,16aH-pyrido[2,1-d]1,5,9-triazacyclotridecan-13-yl]heptan-2-one
CAS Registry NumberNot Available
SMILES
CCCCCC(=O)C[C@@H]1C=CC[C@@H]2CC(=O)NCCCCNCCCN12
InChI Identifier
InChI=1S/C21H37N3O2/c1-2-3-4-11-20(25)16-18-9-7-10-19-17-21(26)23-14-6-5-12-22-13-8-15-24(18)19/h7,9,18-19,22H,2-6,8,10-17H2,1H3,(H,23,26)/t18-,19+/m0/s1
InChI KeyRKTWGMYTKBSCLV-RBUKOAKNSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.92ALOGPS
logP0.59ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.72ChemAxon
pKa (Strongest Basic)10.3ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area64.93 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity108.35 m³·mol⁻¹ChemAxon
Polarizability42.9 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
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. Elsohly MA, Turner CE, Phoebe CH Jr, Knapp JE, Schiff PL Jr, Slatkin DJ: Anhydrocannabisativine, a new alkaloid from Cannabis sativa L. J Pharm Sci. 1978 Jan;67(1):124. doi: 10.1002/jps.2600670135. [PubMed:619102 ]
  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 ]
  3. Ryz NR, Remillard DJ, Russo EB: Cannabis Roots: A Traditional Therapy with Future Potential for Treating Inflammation and Pain. Cannabis Cannabinoid Res. 2017 Aug 1;2(1):210-216. doi: 10.1089/can.2017.0028. eCollection 2017. [PubMed:29082318 ]