IMPPAT Phytochemical information: 
cis-Piperitone oxide

cis-Piperitone oxide
Summary

SMILES: CC([C@@H]1CC[C@]2([C@@H](C1=O)O2)C)C
InChI: InChI=1S/C10H16O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h6-7,9H,4-5H2,1-3H3/t7-,9+,10-/m0/s1
InChIKey: IAFONZHDZMCORS-SFGNSQDASA-N
DeepSMILES: CC[C@@H]CC[C@][C@@H]C6=O))O3))C)))))C
Scaffold Graph/Node/Bond level: O=C1CCCC2OC12
Scaffold Graph/Node level: OC1CCCC2OC12
Scaffold Graph level: CC1CCCC2CC12
Functional groups: C[C@@]1(C)O[C@@H]1C(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Oxepanes
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Menthane monoterpenoids|Monocyclic monoterpenoids
Synonymous chemical names:
cis-piperitone oxide, cis-piperitone epoxide
External chemical identifiers:
CID:CID_6430796; ZINC:ZINC000005647940; FDASRS:N335VVZ43U; SureChEMBL:SCHEMBL909589
Chemical structure download


cis-Piperitone oxide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 168.24
Log P RDKit 1.78
Topological polar surface area (Å2) RDKit 29.6
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.9
Number of rotatable bonds RDKit 1
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 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


cis-Piperitone 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 0.558436


cis-Piperitone oxide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.07
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