IMPPAT Phytochemical information: 
Linoleic acid
Linoleic acid
Summary

SMILES: CCCCC/C=CC/C=CCCCCCCCC(=O)O
InChI: InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
InChIKey: OYHQOLUKZRVURQ-HZJYTTRNSA-N
DeepSMILES: CCCCC/C=CC/C=CCCCCCCCC=O)O
Functional groups: C/C=CC; 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:
(e,e)-9,12-octadecadienoic acid (syn. linoleic acid), (z,z)-9,12-octadecadienoic acid (linoleic acid), (z,z,z)-9,12,15-octadecatrienoic acid (linoleic acid), linoleic, linoleic acid, linoleic acids, linolic acid
External chemical identifiers:
CID:5280450; ChEMBL:CHEMBL267476; ChEBI:17351; ZINC:ZINC000004474613; FDASRS:9KJL21T0QJ; SureChEMBL:SCHEMBL7067; MolPort-001-788-459
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Linoleic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 280.45
Log P RDKit 5.88
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 5
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.72
Number of rotatable bonds RDKit 14
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
Linoleic 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 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 0.3183
Linoleic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -5.74
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Linoleic acid
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000200676CETP843
ENSP00000215885PLA2G3900
ENSP00000216780PCK2862
ENSP00000217233TRIB3900
ENSP00000217964TBL1X900
ENSP00000220584FDFT1907
ENSP00000222002SULT2A1900
ENSP00000222157FGF21800
ENSP00000222381PON1816
ENSP00000222982CYP3A5800
ENSP00000223095SERPINE1823
ENSP00000223190NRF1900
ENSP00000225728MED31900
ENSP00000227665APOA5900
ENSP00000227667APOC3908
ENSP00000232219RBP1900
ENSP00000233242APOB943
ENSP00000236850APOA1981
ENSP00000238651ACOT2800
ENSP00000240055NFYB917
ENSP00000241052CAT904
ENSP00000243077LRP1900
ENSP00000243501PLA2G12A900
ENSP00000246553FFAR1900
ENSP00000247992PLA2G2C900
ENSP00000248041CYP4F11800
ENSP00000251871MED17900
ENSP00000252486APOE916
ENSP00000252595SLC27A1932
ENSP00000252669ACSBG2900
ENSP00000252945CYP2E1900
ENSP00000254351SDC1900
ENSP00000255764MED10900
ENSP00000256104FABP4987
ENSP00000256379MED6900
ENSP00000258648MED4900
ENSP00000258743IL6839
ENSP00000258873ACSBG1900
ENSP00000259407BAAT800
ENSP00000260129TGS1900
ENSP00000260630CYP1B1817
ENSP00000260682CYP2C9900
ENSP00000261523RORA900
ENSP00000262188SMARCD3900
ENSP00000262340RPE65900
ENSP00000262367CREBBP907
ENSP00000262735PPARA992
ENSP00000263205MED15900
ENSP00000263253EP300900
ENSP00000263321TYR842
ENSP00000263390MED26900
ENSP00000263816LRP2900
ENSP00000264039GPC1900
ENSP00000264867PPARGC1A980
ENSP00000265350MED20900
ENSP00000265641CPT1A948
ENSP00000265723ABCB4900
ENSP00000266659GLIPR1900
ENSP00000267842SLC27A2923
ENSP00000268711MED9900
ENSP00000268712NCOR1908
ENSP00000276914PLIN2909
ENSP00000277508PAEP773
ENSP00000278840FADS2957
ENSP00000281455ACSL1912
ENSP00000281928MED13L900
ENSP00000282441YAP1900
ENSP00000282892MED21900
ENSP00000285979CYP2C18800
ENSP00000286317MED7900
ENSP00000287820PPARG953
ENSP00000287936HMGCR945
ENSP00000289416ACSM3900
ENSP00000290472PLA2G4D900
ENSP00000290663MED8900
ENSP00000292035MED27900
ENSP00000292377GPC2900
ENSP00000293761ALOX15977
ENSP00000293777MED11900
ENSP00000294728VCAM1828
ENSP00000295834FABP1912
ENSP00000296861TNFRSF21900
ENSP00000296869ACSL6900
ENSP00000297258FABP5825
ENSP00000297347MED30900
ENSP00000300056PEX11A900
ENSP00000300651MED1913
ENSP00000301146CYP2A7800
ENSP00000301455ANGPTL4981
ENSP00000301645CYP7A1933
ENSP00000301956ACSM1900
ENSP00000302967HDAC3913
ENSP00000303192RGL1900
ENSP00000303634LRP8900
ENSP00000304845UGT1A1800
ENSP00000306245FOS800
ENSP00000307046SDC2900
ENSP00000307821FADS6900
ENSP00000308032CYP2S1800
ENSP00000308165CD36940
ENSP00000308741CLOCK900
ENSP00000309124OLR1897
ENSP00000309259ALAS1900
ENSP00000310701TEAD2900
ENSP00000311095CYP4A11908
ENSP00000311224ACOT1800
ENSP00000312286PLA2G1B932
ENSP00000312649PPARGC1B900
ENSP00000312652LEP866
ENSP00000314343MED29900
ENSP00000315263GLTP800
ENSP00000319814PCK1859
ENSP00000320337PLA2G16900
ENSP00000320940NCOA1900
ENSP00000321821CYP4F12800
ENSP00000322229FADS1955
ENSP00000322706HMGCS1909
ENSP00000322909FHL2900
ENSP00000323071ACOT4800
ENSP00000323720MED14900
ENSP00000324693GRHL1900
ENSP00000325612MED16900
ENSP00000325690CARM1900
ENSP00000326767MED25900
ENSP00000327315TIAM2900
ENSP00000327916ACSM5900
ENSP00000329357SP1900
ENSP00000330442PLB1900
ENSP00000331736SELE822
ENSP00000332679CYP2A13800
ENSP00000333142PLA2G6917
ENSP00000333534CYP2F1800
ENSP00000334246CYP4Z1800
ENSP00000337224LRAT900
ENSP00000337340MED19900
ENSP00000337450CYP3A7800
ENSP00000337915CYP3A4900
ENSP00000338018HIF1A907
ENSP00000338283NPAS2900
ENSP00000339787ACSL4979
ENSP00000340296C10orf129900
ENSP00000342007CYP1A2900
ENSP00000342343MED22900
ENSP00000344468SDC3900
ENSP00000345702NFYA900
ENSP00000345772TEAD3900
ENSP00000346768UGT1A9900
ENSP00000348429ACSL5900
ENSP00000350012ACSL3900
ENSP00000350425APOA4900
ENSP00000351894NCOA6914
ENSP00000352926TEAD4900
ENSP00000353483MAPK8822
ENSP00000353622SIN3A900
ENSP00000353679MME800
ENSP00000353820CYP2D6800
ENSP00000353847WWTR1900
ENSP00000354476SREBF2909
ENSP00000354588TEAD1900
ENSP00000355627AGT907
ENSP00000355996G0S2900
ENSP00000356436PLA2G4A926
ENSP00000356954CTGF900
ENSP00000356969APOA2900
ENSP00000357047MED23900
ENSP00000357907CDK19900
ENSP00000358414HMGCS2911
ENSP00000358719ME1900
ENSP00000359864GPC4909
ENSP00000360247CYP2J2916
ENSP00000360317CYP2C8900
ENSP00000360372CYP2C19900
ENSP00000360541CPT2933
ENSP00000360762ANKRD1900
ENSP00000360968CYP4X1800
ENSP00000360991CYP4B1800
ENSP00000361066NCOA3900
ENSP00000361818SDC4979
ENSP00000362123PLA2G12B900
ENSP00000362948MED18900
ENSP00000363193MED12900
ENSP00000363512ALOX5885
ENSP00000363827HSPG2900
ENSP00000363868ABCA1920
ENSP00000364243PLA2G2F900
ENSP00000364249PLA2G5900
ENSP00000364252PLA2G2A925
ENSP00000364257PLA2G2E900
ENSP00000366246GPC6909
ENSP00000366267GPC5900
ENSP00000367086ACOT7800
ENSP00000368678AGRN900
ENSP00000369050CYP1A1907
ENSP00000369530ALOX15B960
ENSP00000370938CDK8900
ENSP00000371833PLA2G4F900
ENSP00000371886JMJD7-PLA2G4B900
ENSP00000374357ARNTL900
ENSP00000377686MED24900
ENSP00000377836GPC3900
ENSP00000380888MED13900
ENSP00000382349ACSM4900
ENSP00000382434PLA2G4E900
ENSP00000384018NCOR2921
ENSP00000386331MYO7A900
ENSP00000393847PLA2G10909
ENSP00000396045PLA2G4B900
ENSP00000396620NFYC900
ENSP00000398698TNF848
ENSP00000399968NCOA2900
ENSP00000400036PLA2G4C900
ENSP00000405574TBL1XR1900
ENSP00000409612ACADM900
ENSP00000415786SERPINE2786
ENSP00000417401HELZ2900
ENSP00000419692RXRA909
ENSP00000428982CCNC900
ENSP00000434516TXNRD1900
ENSP00000454071LDLR916
ENSP00000455307CHD9900
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.