IMPPAT Phytochemical information: 
Cannabisativine
Cannabisativine
Summary

SMILES: CCCCC[C@H]([C@H]([C@@H]1C=CC[C@@H]2N1CCCNCCCCNC(=O)C2)O)O
InChI: 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
InChIKey: KZZKPJBKEJKNAK-HUUJSLGLSA-N
DeepSMILES: CCCCC[C@H][C@H][C@@H]C=CC[C@@H]N6CCCNCCCCNC=O)C%13)))))))))))))))))O))O
Scaffold Graph/Node/Bond level: O=C1CC2CC=CCN2CCCNCCCCN1
Scaffold Graph/Node level: OC1CC2CCCCN2CCCNCCCCN1
Scaffold Graph level: CC1CCCCCCCCCC2CCCCC2C1
Functional groups: CC=CC; CN(C)C; CNC; CNC(=O)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Macrolactams
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Polyamines
Synonymous chemical names:
cannabisativine
External chemical identifiers:
CID:CID_442846; ChEBI:CHEBI:3361; SureChEMBL:SCHEMBL19877914
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cannabisativine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 381.56
Log P RDKit 1.57
Topological polar surface area (Å2) RDKit 84.83
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.86
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Cannabisativine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.414548
Cannabisativine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.34
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes