IMPPAT Phytochemical information: 
Linolenic acid

Linolenic acid
Summary

SMILES: CC/C=C\C/C=C\C/C=C\CCCCCCCC(=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/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-
InChIKey: DTOSIQBPPRVQHS-PDBXOOCHSA-N
DeepSMILES: CC/C=C\C/C=C\C/C=C\CCCCCCCC=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:
linolenic acid, alpha-, linolenic acid, α-linolenic acid, linolenate, linolenic acid, alpha, Linolenic Acid
External chemical identifiers:
CID:CID_5280934; ChEMBL:CHEMBL8739; ChEBI:CHEBI:27432; ZINC:ZINC000003802189; FDASRS:0RBV727H71; SureChEMBL:SCHEMBL15282; MolPort-003-937-817
Chemical structure download


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


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


Linolenic acid
ADME 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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -2.60
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


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_000627ENSG00000102539MLNR2862ChEMBL
TAR_EXP_000608ENSG00000115419GLS2744ChEMBL, NPASS
TAR_EXP_000578ENSG00000121853GHSR2693ChEMBL
TAR_EXP_000572ENSG00000108773KAT2A2648ChEMBL, NPASS
TAR_EXP_000559ENSG00000185513L3MBTL126013NPASS
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_000285ENSG00000137869CYP19A11588BindingDB, ChEMBL, NPASS
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000330ENSG00000144891AGTR1185ChEMBL
TAR_EXP_000339ENSG00000151617EDNRA1909ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000367ENSG00000112759SLC29A12030ChEMBL
TAR_EXP_000407ENSG00000117525F32152BindingDB, ChEMBL, NPASS
TAR_EXP_000408ENSG00000057593F72155ChEMBL
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL, NPASS
TAR_EXP_000458ENSG00000168397ATG4B23192BindingDB, ChEMBL, NPASS
TAR_EXP_000503ENSG00000161905ALOX15246ChEMBL, NPASS
TAR_EXP_000504ENSG00000179593ALOX15B247ChEMBL, NPASS
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000361ENSG00000128394APOBEC3F200316NPASS
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL, NPASS
TAR_EXP_001061ENSG00000113448PDE4D5144ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_001129ENSG00000170890PLA2G1B5319BindingDB, NPASS
TAR_EXP_001139ENSG00000166851PLK15347NPASS
TAR_EXP_001151ENSG00000170734POLH5429ChEMBL, NPASS
TAR_EXP_001166ENSG00000186951PPARA5465ChEMBL, NPASS
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_000628ENSG00000126266FFAR12864ChEMBL, NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000720ENSG00000106211HSPB13315NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000744ENSG00000186188FFAR4338557BindingDB, ChEMBL, NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL
TAR_EXP_000814ENSG00000108424KPNB13837NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_001171ENSG00000132170PPARG5468BindingDB, ChEMBL, NPASS
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_001599ENSG00000164362TERT7015ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001485ENSG00000197299BLM641NPASS
TAR_EXP_001676ENSG00000165392WRN7486ChEMBL, NPASS
TAR_EXP_001836ENSG00000144852NR1I28856ChEMBL, NPASS
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_001839ENSG00000110148CCKBR887ChEMBL
TAR_EXP_001942ENSG00000012504NR1H49971NPASS
TAR_EXP_001170ENSG00000112033PPARD5467ChEMBL, NPASS
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_001810ENSG00000067955CBFB865NPASS
TAR_EXP_001461ENSG00000186350RXRA6256NPASS
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL, NPASS
TAR_EXP_001373ENSG00000239713APOBEC3G60489NPASS
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_000119ENSG00000101751POLI11201ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_001190ENSG00000126895AVPR2554ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL, NPASS
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL, NPASS
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_000017ENSG00000169371SNUPN10073NPASS