IMPPAT Phytochemical information: 
gamma-Linolenic acid
gamma-Linolenic acid
Summary

SMILES: CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O
InChI: InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-
InChIKey: VZCCETWTMQHEPK-QNEBEIHSSA-N
DeepSMILES: CCCCC/C=C\C/C=C\C/C=C\CCCCC=O)O
Functional groups: 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: Lineolic acids and derivatives
NP Classifier Biosynthetic pathway: Fatty acids
NP Classifier Superclass: Fatty Acids and Conjugates
NP Classifier Class: Unsaturated fatty acids
Synonymous chemical names:
gamma-linolenic acid, octadeca-6,9,12-trienoic acid, γ-linolenic acid, octadeca-6,9,12- trienoic acid
External chemical identifiers:
CID:CID_5280933; ChEMBL:CHEMBL464982; ChEBI:CHEBI:28661; ZINC:ZINC000003777423; FDASRS:78YC2MAX4O; SureChEMBL:SCHEMBL19418; MolPort-003-937-818
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
gamma-Linolenic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 278.44
Log P RDKit 5.66
Topological polar surface area (Å2) RDKit 37.3
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
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
gamma-Linolenic acid
Drug-likeness
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 1
Ghose filter RDKit Failed
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 0.34841
gamma-Linolenic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -5.40
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
gamma-Linolenic acid
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001556ENSG00000277893SRD5A26716BindingDB, ChEMBL, NPASS
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_001171ENSG00000132170PPARG5468BindingDB, ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL, NPASS
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_001676ENSG00000165392WRN7486NPASS
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000119ENSG00000101751POLI11201ChEMBL, NPASS
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_001759ENSG00000138794CASP6839ChEMBL, NPASS
TAR_EXP_001170ENSG00000112033PPARD5467ChEMBL, NPASS
TAR_EXP_000408ENSG00000057593F72155ChEMBL
TAR_EXP_001151ENSG00000170734POLH5429ChEMBL, NPASS
TAR_EXP_000424ENSG00000169710FASN2194ChEMBL, NPASS
TAR_EXP_000559ENSG00000185513L3MBTL126013NPASS
TAR_EXP_000572ENSG00000108773KAT2A2648ChEMBL, NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000628ENSG00000126266FFAR12864ChEMBL, NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000407ENSG00000117525F32152BindingDB, ChEMBL, NPASS
TAR_EXP_000773ENSG00000169083AR367ChEMBL
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL
TAR_EXP_000810ENSG00000128052KDR3791ChEMBL
TAR_EXP_001166ENSG00000186951PPARA5465ChEMBL, NPASS
TAR_EXP_000747ENSG00000138413IDH13417NPASS
TAR_EXP_000405ENSG00000180210F22147ChEMBL
TAR_EXP_001139ENSG00000166851PLK15347NPASS
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000881ENSG00000087085ACHE43ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001056ENSG00000065989PDE4A5141ChEMBL
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL, NPASS