IMPPAT Phytochemical information: 
(-)-Vernolic acid
(-)-Vernolic acid
Summary

SMILES: CCCCC[C@@H]1O[C@@H]1C/C=CCCCCCCCC(=O)O
InChI: InChI=1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m0/s1
InChIKey: CCPPLLJZDQAOHD-BEBBCNLGSA-N
DeepSMILES: CCCCC[C@@H]O[C@@H]3C/C=CCCCCCCCC=O)O
Scaffold Graph/Node/Bond level: C1CO1
Scaffold Graph/Node level: C1CO1
Scaffold Graph level: C1CC1
Functional groups: C/C=CC; CC(=O)O; C[C@@H]1O[C@@H]1C
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
NP Classifier Class: Epoxy fatty acids
Synonymous chemical names:
cis-12,13-epoxy-cis-9-octadecenoic acid
External chemical identifiers:
CID:5281128; ChEBI:38300; ZINC:ZINC000004097549; FDASRS:FF156V3318; SureChEMBL:SCHEMBL2507620
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(-)-Vernolic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 296.45
Log P RDKit 5.1
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 3
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.83
Number of rotatable bonds RDKit 14
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
(-)-Vernolic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 0.2756
(-)-Vernolic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.15
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 2.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
(-)-Vernolic acid
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000221730EPHX3900
ENSP00000222982CYP3A5800
ENSP00000248041CYP4F11800
ENSP00000260630CYP1B1800
ENSP00000272167EPHX1914
ENSP00000285979CYP2C18800
ENSP00000301146CYP2A7800
ENSP00000308032CYP2S1800
ENSP00000321821CYP4F12800
ENSP00000332679CYP2A13800
ENSP00000333534CYP2F1800
ENSP00000334246CYP4Z1800
ENSP00000337450CYP3A7800
ENSP00000342007CYP1A2800
ENSP00000353820CYP2D6800
ENSP00000359410EPHX4900
ENSP00000360247CYP2J2800
ENSP00000360317CYP2C8800
ENSP00000360968CYP4X1800
ENSP00000360991CYP4B1800
ENSP00000369050CYP1A1800
ENSP00000430269EPHX2900
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.