IMPPAT Phytochemical information: 
(9Z,12Z)-15,16-Epoxy-9,12-octadecadienoic acid
(9Z,12Z)-15,16-Epoxy-9,12-octadecadienoic acid
Summary

SMILES: CCC1OC1C/C=C/C/C=C/CCCCCCCC(=O)O
InChI: InChI=1S/C18H30O3/c1-2-16-17(21-16)14-12-10-8-6-4-3-5-7-9-11-13-15-18(19)20/h4,6,10,12,16-17H,2-3,5,7-9,11,13-15H2,1H3,(H,19,20)/b6-4+,12-10+
InChIKey: HKSDVVJONLXYKL-QGCGKJESSA-N
DeepSMILES: CCCOC3C/C=C/C/C=C/CCCCCCCC=O)O
Scaffold Graph/Node/Bond level: C1CO1
Scaffold Graph/Node level: C1CO1
Scaffold Graph level: C1CC1
Functional groups: CC1OC1C; C/C=C/C; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Fatty Acyls
ClassyFire Subclass: Fatty acids and conjugates
NP Classifier Biosynthetic pathway: Fatty acids
NP Classifier Superclass: Fatty Acids and Conjugates|Octadecanoids
NP Classifier Class: Epoxy fatty acids|Other Octadecanoids
Synonymous chemical names:
15,16-epoxy-9,12-octadecadienoic acid
External chemical identifiers:
CID:CID_14212253; SureChEMBL:SCHEMBL3741569
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(9Z,12Z)-15,16-Epoxy-9,12-octadecadienoic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 294.44
Log P RDKit 4.87
Topological polar surface area (Å2) RDKit 49.83
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.72
Number of rotatable bonds RDKit 13
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1
(9Z,12Z)-15,16-Epoxy-9,12-octadecadienoic acid
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 Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.299302
(9Z,12Z)-15,16-Epoxy-9,12-octadecadienoic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.50
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No