IMPPAT Phytochemical information: 
Isocannabispiran

Isocannabispiran
Summary

SMILES: COc1cc(O)cc2c1C1(CCC(=O)CC1)CC2
InChI: InChI=1S/C15H18O3/c1-18-13-9-12(17)8-10-2-5-15(14(10)13)6-3-11(16)4-7-15/h8-9,17H,2-7H2,1H3
InChIKey: ZKJMXTKGSQHXEC-UHFFFAOYSA-N
DeepSMILES: COcccO)ccc6CCCC=O)CC6)))))CC5
Scaffold Graph/Node/Bond level: O=C1CCC2(CC1)CCc1ccccc12
Scaffold Graph/Node level: OC1CCC2(CC1)CCC1CCCCC12
Scaffold Graph level: CC1CCC2(CC1)CCC1CCCCC12
Functional groups: cOC; CC(=O)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Indanes
ClassyFire Subclass: Indan-1-spirocyclohexanes
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
isocannabispiran
Chemical structure download


Isocannabispiran
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 246.31
Log P RDKit 2.73
Topological polar surface area (Å2) RDKit 46.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Isocannabispiran
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.828385


Isocannabispiran
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.14
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes