IMPPAT Phytochemical information: 
Isocaryophyllene oxide
Isocaryophyllene oxide
Summary

SMILES: C=C1CC[C@@H]2O[C@@]2(CC[C@@H]2[C@@H]1CC2(C)C)C
InChI: InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,15-/m1/s1
InChIKey: NVEQFIOZRFFVFW-GUIRCDHDSA-N
DeepSMILES: C=CCC[C@@H]O[C@@]3CC[C@@H][C@@H]%10CC4C)C)))))))C
Scaffold Graph/Node/Bond level: C=C1CCC2OC2CCC2CCC12
Scaffold Graph/Node level: CC1CCC2OC2CCC2CCC12
Scaffold Graph level: CC1CCC2CC2CCC2CCC12
Functional groups: C=C(C)C; C[C@@H]1O[C@]1(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesquiterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Caryophyllane sesquiterpenoids
Synonymous chemical names:
Isocaryophyllene oxide, (1R,4R,5R,9S)-4,5-epoxycaryophyllan-8(13)-ene
External chemical identifiers:
CID:CID_1742211; ChEMBL:CHEMBL399036; ZINC:ZINC000002083321; SureChEMBL:SCHEMBL24110084
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Isocaryophyllene oxide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 220.36
Log P RDKit 3.94
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 4
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.87
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
Isocaryophyllene oxide
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 0.444835
Isocaryophyllene oxide
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 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