IMPPAT Phytochemical information: 
12-Acetoxycaryophyllene-4,5-epoxide

12-Acetoxycaryophyllene-4,5-epoxide
Summary

SMILES: CC(=O)OCC1CCC2OC2(CCC2C1CC2(C)C)C
InChI: InChI=1S/C17H28O3/c1-11(18)19-10-12-5-6-15-17(4,20-15)8-7-14-13(12)9-16(14,2)3/h12-15H,5-10H2,1-4H3
InChIKey: JXTAVNIIVRAIGB-UHFFFAOYSA-N
DeepSMILES: CC=O)OCCCCCOC3CCCC%10CC4C)C)))))))C
Scaffold Graph/Node/Bond level: C1CC2CCC2CCC2OC2C1
Scaffold Graph/Node level: C1CC2CCC2CCC2OC2C1
Scaffold Graph level: C1CC2CCC2CCC2CC2C1
Functional groups: COC(C)=O; CC1OC1(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:
12-acetoxycaryophyllene-4,5-epoxide
External chemical identifiers:
CID:CID_6429035
Chemical structure download


12-Acetoxycaryophyllene-4,5-epoxide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 280.41
Log P RDKit 3.56
Topological polar surface area (Å2) RDKit 38.83
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.94
Number of rotatable bonds RDKit 3
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


12-Acetoxycaryophyllene-4,5-epoxide
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 0.573243


12-Acetoxycaryophyllene-4,5-epoxide
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 -5.50
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 No