IMPPAT Phytochemical information: 
beta-Caryophyllone

beta-Caryophyllone
Summary

SMILES: O=C1CC[C@@]2(C[C@H]1[C@@H]1CC([C@H]1CC2)(C)C)C
InChI: InChI=1S/C15H24O/c1-14(2)8-10-11-9-15(3,6-4-12(10)14)7-5-13(11)16/h10-12H,4-9H2,1-3H3/t10-,11-,12-,15+/m0/s1
InChIKey: JLZBTPJKBKNFEG-JUFZMCDQSA-N
DeepSMILES: O=CCC[C@@]C[C@H]6[C@@H]CC[C@H]4CC9)))C)C))))))C
Scaffold Graph/Node/Bond level: O=C1CCC2CCC3CCC3C1C2
Scaffold Graph/Node level: OC1CCC2CCC3CCC3C1C2
Scaffold Graph level: CC1CCC2CCC3CCC3C1C2
Functional groups: CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbonyl compounds
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Caryophyllane sesquiterpenoids
Synonymous chemical names:
caryophyllone, beta-caryophyllone
External chemical identifiers:
CID:CID_163796
Chemical structure download


beta-Caryophyllone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 220.36
Log P RDKit 3.82
Topological polar surface area (Å2) RDKit 17.07
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 1
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.93
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
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 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


beta-Caryophyllone
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 0.61


beta-Caryophyllone
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 -4.83
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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