IMPPAT Phytochemical information: 
Acetic acid [(1R,9S)-11,11-dimethyl-8-methylenebicyclo[7.2.0]undeca-4-ene-4-yl]methyl ester
Acetic acid [(1R,9S)-11,11-dimethyl-8-methylenebicyclo[7.2.0]undeca-4-ene-4-yl]methyl ester
Summary

SMILES: CC(=O)OC/C/1=C/CCC(=C)[C@@H]2[C@@H](CC1)C(C2)(C)C
InChI: InChI=1S/C17H26O2/c1-12-6-5-7-14(11-19-13(2)18)8-9-16-15(12)10-17(16,3)4/h7,15-16H,1,5-6,8-11H2,2-4H3/b14-7+/t15-,16-/m1/s1
InChIKey: XLKYRVILZQUEJC-DJYJQHBUSA-N
DeepSMILES: CC=O)OC/C=C/CCC=C)[C@@H][C@@H]CC\9))CC4)C)C
Scaffold Graph/Node/Bond level: C=C1CCC=CCCC2CCC12
Scaffold Graph/Node level: CC1CCCCCCC2CCC12
Scaffold Graph level: CC1CCCCCCC2CCC12
Functional groups: COC(C)=O; C/C=C(/C)C; 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-acetoxy-β-caryophyllene
External chemical identifiers:
CID:CID_102006021
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Acetic acid [(1R,9S)-11,11-dimethyl-8-methylenebicyclo[7.2.0]undeca-4-ene-4-yl]methyl ester
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 262.39
Log P RDKit 4.27
Topological polar surface area (Å2) RDKit 26.3
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.71
Number of rotatable bonds RDKit 3
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 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Acetic acid [(1R,9S)-11,11-dimethyl-8-methylenebicyclo[7.2.0]undeca-4-ene-4-yl]methyl ester
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.55
Acetic acid [(1R,9S)-11,11-dimethyl-8-methylenebicyclo[7.2.0]undeca-4-ene-4-yl]methyl ester
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 -5.27
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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