IMPPAT Phytochemical information: 
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid
Summary

SMILES: CC/C=C/C/C=C/C=C/C(CCCCCCCC(=O)O)O
InChI: InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,6,8,11,14,17,19H,2,5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3+,8-6+,14-11+
InChIKey: RIGGEAZDTKMXSI-JPAZTHTMSA-N
DeepSMILES: CC/C=C/C/C=C/C=C/CCCCCCCCC=O)O)))))))))O
Functional groups: C/C=C/C; C/C=C/C=C/C; CC(=O)O; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Fatty Acyls
ClassyFire Subclass: Lineolic acids and derivatives
NP Classifier Biosynthetic pathway: Fatty acids
NP Classifier Superclass: Octadecanoids
NP Classifier Class: Other Octadecanoids
Synonymous chemical names:
(9S, 10E, 12Z, 15Z)-9-hydroxy-10, 12, 15-octadecatrienoic acid, (9s,10e,12,15z)-9-hydroxy-10,12,15-octadecatrienoic acid, (9s, 10e, 12z, 15z)-9-hydroxy-10, 12, 15-octadecatrienoic acid
External chemical identifiers:
CID:CID_13917187; ChEBI:CHEBI:89388; SureChEMBL:SCHEMBL10720877
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 294.44
Log P RDKit 4.63
Topological polar surface area (Å2) RDKit 57.53
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
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 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.61
Number of rotatable bonds RDKit 13
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 0
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 0
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic 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 0.295625
(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -4.79
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