IMPPAT Phytochemical information: 
(-)-Kessane

(-)-Kessane
Summary

SMILES: C[C@@H]1CC[C@@H]2[C@@H]1C[C@@H]1CC2(C)OC1(C)C
InChI: InChI=1S/C14H24O/c1-9-5-6-12-11(9)7-10-8-14(12,4)15-13(10,2)3/h9-12H,5-8H2,1-4H3/t9-,10-,11-,12-,14?/m1/s1
InChIKey: WBHXSKHCVPVDDZ-WJVRHOARSA-N
DeepSMILES: C[C@@H]CC[C@@H][C@@H]5C[C@@H]CC6C)OC5C)C
Scaffold Graph/Node/Bond level: C1CC2CC3COC(C3)C2C1
Scaffold Graph/Node level: C1CC2CC3COC(C3)C2C1
Scaffold Graph level: C1CC2CC3CCC(C3)C2C1
Functional groups: COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Oxepanes
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Guaiane sesquiterpenoids
Synonymous chemical names:
(–)-kessane
External chemical identifiers:
CID:CID_91749835
Chemical structure download


(-)-Kessane
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 208.35
Log P RDKit 3.63
Topological polar surface area (Å2) RDKit 9.23
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 15
Number of heteroatoms RDKit 1
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.36
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 1
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


(-)-Kessane
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.59


(-)-Kessane
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.12
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No