IMPPAT Phytochemical information: 
(2S,3S)-2-methyl-3-(3-methylbut-2-enyl)-2-(4-methylcyclohex-3-en-1-yl)oxirane

(2S,3S)-2-methyl-3-(3-methylbut-2-enyl)-2-(4-methylcyclohex-3-en-1-yl)oxirane
Summary

SMILES: CC(=CC[C@@H]1O[C@@]1(C)C1CCC(=CC1)C)C
InChI: InChI=1S/C15H24O/c1-11(2)5-10-14-15(4,16-14)13-8-6-12(3)7-9-13/h5-6,13-14H,7-10H2,1-4H3/t13?,14-,15-/m0/s1
InChIKey: PBNXUEQZNAEDOI-FGRDXJNISA-N
DeepSMILES: CC=CC[C@@H]O[C@@]3C)CCCC=CC6))C))))))))))C
Scaffold Graph/Node/Bond level: C1=CCC(C2CO2)CC1
Scaffold Graph/Node level: C1CCC(C2CO2)CC1
Scaffold Graph level: C1CCC(C2CC2)CC1
Functional groups: CC=C(C)C; C[C@@H]1O[C@@]1(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Epoxides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Bisabolane sesquiterpenoids
Synonymous chemical names:
bisabolene epoxide
External chemical identifiers:
CID:CID_91753445
Chemical structure download


(2S,3S)-2-methyl-3-(3-methylbut-2-enyl)-2-(4-methylcyclohex-3-en-1-yl)oxirane
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 220.36
Log P RDKit 4.25
Topological polar surface area (Å2) RDKit 12.53
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 1
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.73
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
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


(2S,3S)-2-methyl-3-(3-methylbut-2-enyl)-2-(4-methylcyclohex-3-en-1-yl)oxirane
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.511536


(2S,3S)-2-methyl-3-(3-methylbut-2-enyl)-2-(4-methylcyclohex-3-en-1-yl)oxirane
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 -4.94
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No