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Compound Detail

CHEMBL267476

LINOLEIC ACID
🧪 Phase II
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🧪 Phase II
CCCCC/C=C\C/C=C\CCCCCCCC(=O)O

Basic Information

ChEMBL ID CHEMBL267476
Name LINOLEIC ACID
Phase Phase II
Structure Type MOL
InChI Key OYHQOLUKZRVURQ-HZJYTTRNSA-N

Known Names

9,12-linoleic acid C18:2 (n-6) Emersol 315 FEMA NO. 3380, LINOLEIC ACID- Linoleate Linoleic acid Linoleic acid component of vitamin f Linolic acid NSC-281243 Polylin 515 Ronacare asc 3 Unifac 6550
19
Targets
43
Activities
4
Assay Types
0
PK Parameters
20
Publications
12
Known Names
5
Indications

Molecular Properties

280.4
MW (Da)
5.88
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.32
QED
1
Ro5 Violations
14
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem deu-

Extended Properties

Molecular Formula C18H32O2
MW 280.45
Aromatic Rings 0
Heavy Atoms 20
NP-Likeness 1.19

Indications

Obesity Asthma Diabetes Mellitus, Type 2 Neoplasms Breast Neoplasms

Activity Summary

IC50 26 meas. best 6.16
EC50 13 meas. best 6.5
Kd 2 meas. best 8.32
Ki 2 meas. best 5.17

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Peroxisome proliferator-activated receptor alpha
CHEMBL239
Kd 8.32 8.32 4.8 1
Free fatty acid receptor 4
CHEMBL5339
EC50 6.5 6.5 316.2 1
Free fatty acid receptor 1
CHEMBL4422
EC50 6.27 5.7729 540.0 7
Aldo-keto reductase family 1 member C3
CHEMBL4681
IC50 6.16 6.16 690.0 2
Fatty acid-binding protein, adipocyte
CHEMBL2083
IC50 6.0 5.2067 1000.0 3
Seed linoleate 13S-lipoxygenase-1
CHEMBL4586
IC50 6.0 5.2833 1000.0 3
Fatty acid-binding protein, heart
CHEMBL3344
IC50 6.0 6.0 1000.0 3
Peroxisome proliferator-activated receptor alpha
CHEMBL239
IC50 5.96 5.96 1100.0 2
Peroxisome proliferator-activated receptor gamma
CHEMBL235
IC50 5.21 5.21 6200.0 1
Fatty acid-binding protein, adipocyte
CHEMBL2083
Ki 5.17 5.17 6800.0 1
Unchecked
CHEMBL612545
EC50 5.16 5.16 6918.3 1
Fatty acid-binding protein, heart
CHEMBL3344
Ki 5.03 5.03 9300.0 1
Peroxisome proliferator-activated receptor delta
CHEMBL3979
IC50 5.0 5.0 10000.0 1
GPR40-Galpha16
CHEMBL5482994
EC50 5.0 5.0 10100.0 1
Prostaglandin G/H synthase 1
CHEMBL221
IC50 4.89 4.89 13000.0 1
Hepatitis C virus
CHEMBL379
EC50 4.7 4.7 20200.0 1
Unchecked
CHEMBL612545
IC50 4.57 4.4967 27000.0 3
Coagulation factor VII/tissue factor
CHEMBL2095194
IC50 4.39 4.39 41000.0 1
Aromatase
CHEMBL1978
IC50 4.32 4.32 48000.0 1
Nuclear receptor subfamily 4 group A member 2
CHEMBL5002
Kd 4.3 4.3 50000.0 1
Adenosine receptor A1
CHEMBL318
IC50 4.19 4.19 65000.0 1
Prostaglandin G/H synthase 2
CHEMBL4102
IC50 4.03 4.03 94000.0 1
NAD-dependent protein deacylase sirtuin-6
CHEMBL2163182
EC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Peroxisome proliferator-activated receptor alpha Kd = 4.8 nM 8.32 Binding affinity to PPAR-alpha (unknown origin) by fluorescence-based assay -
Free fatty acid receptor 4 EC50 = 316.23 nM 6.5 Agonist activity at human FFA4 receptor expressed in U2OS cells assessed as calc... 24881566
Free fatty acid receptor 1 EC50 = 540.0 nM 6.27 Agonist activity at human GPR40 expressed in CHOK1 cells by fluorescence assay 18993064
Free fatty acid receptor 1 EC50 = 540.0 nM 6.27 Agonist activity at GPR40 18993064
Free fatty acid receptor 1 EC50 = 549.54 nM 6.26 Agonist activity at human GPR40 expressed in CHOK1 cells by fluorescence assay 18993064
Aldo-keto reductase family 1 member C3 IC50 = 690.0 nM 6.16 Inhibition of human AKR1C3 expressed in Escherichia coli BL21(DE3) pLysS cells u... 32463235
Aldo-keto reductase family 1 member C3 IC50 = 690.0 nM 6.16 Inhibition of human AKR1C3 expressed in Escherichia coli BL21(DE3) pLysS cells u... 32463235
Fatty acid-binding protein, heart IC50 = 1000.0 nM 6.0 Inhibition of FABP3 (unknown origin) relative to linoleic acid 25461324
Fatty acid-binding protein, heart IC50 = 1000.0 nM 6.0 Inhibition of FABP4 (unknown origin) relative to linoleic acid 25461324
Fatty acid-binding protein, adipocyte IC50 = 1000.0 nM 6.0 Displacement of 8-anilino-1-naphthalene-sulfonic acid from human His-FABP4 expre... 20471252
Fatty acid-binding protein, heart IC50 = 1000.0 nM 6.0 Displacement of 8-anilino-1-naphthalene-sulfonic acid from human His-FABP3 expre... 20471252
Seed linoleate 13S-lipoxygenase-1 IC50 = 1000.0 nM 6.0 Allosteric inhibition of soybean LO1 19716306
Peroxisome proliferator-activated receptor alpha IC50 = 1100.0 nM 5.96 Inhibition of PPAR-alpha (unknown origin) by SPA assay -
Peroxisome proliferator-activated receptor alpha IC50 = 1100.0 nM 5.96 Displacement of [3H]GW2331 from Homo sapiens (human) PPARalpha receptor by scint... -
Free fatty acid receptor 1 EC50 = 1800.0 nM 5.75 Agonist activity at human GPR40 expressed in CHO cells assessed as calcium flux ... 18993064
Free fatty acid receptor 1 EC50 = 4800.0 nM 5.32 Agonist activity at human FFA1 receptor expressed in HEK293 cells assessed as in... 30685095
Free fatty acid receptor 1 EC50 = 4800.0 nM 5.32 Agonist activity at human GPR40 expressed in human HEK293 cells assessed as incr... 30392954
Free fatty acid receptor 1 EC50 = 6043.0 nM 5.22 Agonist activity at human GPR40 expressed in HEK293 cells by Fluo4-AM dye based ... 36933395
Peroxisome proliferator-activated receptor gamma IC50 = 6200.0 nM 5.21 Displacement of [3H]BRL49653 from Homo sapiens (human) PPARgamma receptor by sci... -
Fatty acid-binding protein, adipocyte Ki = 6800.0 nM 5.17 Displacement of 1,8-ANS from His6-tagged FABP4 (unknown origin) expressed in Esc... 27460668

Literature References

PubMed DOI Target Context # Activities
21780738 10.1021/jf201611b Heterodera zeae 20
23121218 10.1021/jf3036885 Meloidogyne incognita 18
17954701 10.1128/aac.01009-07 Unchecked 7
10395519 10.1021/np9805490 Unchecked 6
18993064 10.1016/j.bmcl.2008.10.085 Free fatty acid receptor 1 6
20471252 10.1016/j.bmcl.2010.04.095 Unchecked 6
17420205 10.1128/aac.01426-06 Hepatitis C virus 6
9834151 10.1021/np980117p Unchecked 5
18044832 10.1021/jf072548w Coptotermes formosanus 5
10395519 10.1021/np9805490 Adenosine receptor A1 5
18044832 10.1021/jf072548w Lactuca sativa 4
34213345 10.1021/acs.jmedchem.1c00601 NAD-dependent protein deacylase sirtuin-6 4
21903399 10.1016/j.bmc.2011.08.023 Unchecked 4
17420205 10.1128/aac.01426-06 ADMET 3
20471252 10.1016/j.bmcl.2010.04.095 Fatty acid-binding protein, adipocyte 3
15261286 10.1016/j.bmcl.2004.05.086 Sterol O-acyltransferase 1 3
22459211 10.1016/j.bmc.2012.02.039 Unchecked 3
18044832 10.1021/jf072548w Agrostis stolonifera 3
16643058 10.1021/np050513p Aromatase 3
21903399 10.1016/j.bmc.2011.08.023 RAW264.7 3

Data from ChEMBL 36 via Core Engine