IMPPAT Phytochemical information: 
14-Hydroxy-4,5-dihydro-beta-caryophyllene
14-Hydroxy-4,5-dihydro-beta-caryophyllene
Summary

SMILES: OC[C@H]1CCCC(=C)[C@@H]2[C@@H](CC1)C(C2)(C)C
InChI: InChI=1S/C15H26O/c1-11-5-4-6-12(10-16)7-8-14-13(11)9-15(14,2)3/h12-14,16H,1,4-10H2,2-3H3/t12-,13+,14+/m0/s1
InChIKey: QPKKKWDNDWSIRV-BFHYXJOUSA-N
DeepSMILES: OC[C@H]CCCC=C)[C@@H][C@@H]CC9))CC4)C)C
Scaffold Graph/Node/Bond level: C=C1CCCCCCC2CCC12
Scaffold Graph/Node level: CC1CCCCCCC2CCC12
Scaffold Graph level: CC1CCCCCCC2CCC12
Functional groups: CO; C=C(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:
14-hydroxy-4,5-dihydro-β-caryophyllene
External chemical identifiers:
CID:CID_10036514; ChEMBL:CHEMBL501643; ZINC:ZINC000014920590
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
14-Hydroxy-4,5-dihydro-beta-caryophyllene
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 222.37
Log P RDKit 3.78
Topological polar surface area (Å2) RDKit 20.23
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
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 2
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.87
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
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 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
14-Hydroxy-4,5-dihydro-beta-caryophyllene
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 0.669447
14-Hydroxy-4,5-dihydro-beta-caryophyllene
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 -4.88
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No