Showing Compound Card for cannabisativine (CDB000233)

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Record Information
Version1.0
Created at2020-03-19 00:25:54 UTC
Updated at2020-12-07 19:07:17 UTC
CannabisDB IDCDB000233
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namecannabisativine
DescriptionCannabisativine belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturations or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the nitrogen atom replacing the oxigen atom of the cyclic ester group) of the naturally occurring macrolides. Cannabisativine is an alkaloid isolated from the roots of Cannabis sativa L. and its structure was established by single crystal X-ray analysis (PMID: 957120 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC21H39N3O3
Average Molecular Weight381.56
Monoisotopic Molecular Weight381.2991
IUPAC Name(1S,2R)-1-[(13S,16aS)-2-hydroxy-1H,4H,5H,6H,7H,8H,9H,10H,11H,13H,16H,16aH-pyrido[2,1-d]1,5,9-triazacyclotridecan-13-yl]heptane-1,2-diol
Traditional Namecannabisativine
CAS Registry Number57682-64-1
SMILES
CCCCC[C@@H](O)[C@@H](O)[C@@H]1C=CC[C@H]2C\C(O)=N/CCCCNCCCN12
InChI Identifier
InChI=1S/C21H39N3O3/c1-2-3-4-11-19(25)21(27)18-10-7-9-17-16-20(26)23-14-6-5-12-22-13-8-15-24(17)18/h7,10,17-19,21-22,25,27H,2-6,8-9,11-16H2,1H3,(H,23,26)/t17-,18-,19+,21-/m0/s1
InChI KeyKZZKPJBKEJKNAK-HUUJSLGLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolactams
Sub ClassNot Available
Direct ParentMacrolactams
Alternative Parents
Substituents
  • Macrolactam
  • 1,3-aminoalcohol
  • 1,2-diol
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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
logP1.64ALOGPS
logP-0.55ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.69ChemAxon
pKa (Strongest Basic)10.4ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area88.32 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity110.59 m³·mol⁻¹ChemAxon
Polarizability44.76 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
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 IDC00002320
Chemspider IDNot Available
KEGG Compound IDC10576
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442846
PDB IDNot Available
ChEBI ID3361
References
General References
  1. Turner CE, Hsu MH, Knapp JE, Schiff PL Jr, Slatkin DJ: Isolation of cannabisativine, an alkaloid, from Cannabis sativa L. root. J Pharm Sci. 1976 Jul;65(7):1084-5. doi: 10.1002/jps.2600650736. [PubMed:957120 ]
  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 ]