Compound Detail

CHEMBL8739

LINOLENIC ACID

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CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL8739
Name	LINOLENIC ACID
Phase	Preclinical
Structure Type	MOL
InChI Key	DTOSIQBPPRVQHS-PDBXOOCHSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

278.4

MW (Da)

5.66

ALogP

HBA

HBD

37.3

PSA (Å²)

0.35

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C18H30O2
MW	278.44
Aromatic Rings	0
Heavy Atoms	20
NP-Likeness	1.36

Activity Summary

IC50 15 meas. best 5.92

EC50 9 meas. best 8.7

Kd 2 meas. best 8.1

Ki 1 meas. best 5.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Nuclear receptor subfamily 1 group I member 2 CHEMBL3401	EC50	8.7	7.15	2.0	2
Peroxisome proliferator-activated receptor alpha CHEMBL239	Kd	8.1	8.1	7.9	1
Peroxisome proliferator-activated receptor alpha CHEMBL239	IC50	5.92	5.92	1200.0	2
Peroxisome proliferator-activated receptor gamma CHEMBL235	Kd	5.7	5.7	2000.0	1
Free fatty acid receptor 4 CHEMBL5339	EC50	5.58	5.535	2600.0	2
Free fatty acid receptor 1 CHEMBL4422	EC50	5.54	5.36	2884.0	5
Prostaglandin G/H synthase 1 CHEMBL221	Ki	5.4	5.4	4000.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	IC50	5.22	5.22	6000.0	1
Prostaglandin G/H synthase 2 CHEMBL4102	IC50	4.92	4.92	12000.0	1
Cysteine protease ATG4B CHEMBL1741221	IC50	4.82	4.82	15300.0	1
Peroxisome proliferator-activated receptor delta CHEMBL3979	IC50	4.8	4.8	16000.0	1
Unchecked CHEMBL612545	IC50	4.72	4.5467	19000.0	3
Phospholipase A2 CHEMBL4426	IC50	4.65	4.65	22300.0	1
Coagulation factor VII/tissue factor CHEMBL2095194	IC50	4.52	4.52	30000.0	1
Aromatase CHEMBL1978	IC50	4.36	4.36	44200.0	1
Prostaglandin G/H synthase 1 CHEMBL2860	IC50	4.03	4.03	93000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Nuclear receptor subfamily 1 group I member 2	EC50	=	2.0	nM	8.7	Activation of human PXR expressed in human HepG2 (DPX-2) cells assessed as induc...	20966043
Peroxisome proliferator-activated receptor alpha	Kd	=	7.9	nM	8.1	Binding affinity to PPAR-alpha (unknown origin) by fluorescence-based assay	-
Peroxisome proliferator-activated receptor alpha	IC50	=	1200.0	nM	5.92	Inhibition of PPAR-alpha (unknown origin) by SPA assay	-
Peroxisome proliferator-activated receptor alpha	IC50	=	1200.0	nM	5.92	Displacement of [3H]GW2331 from Homo sapiens (human) PPARalpha receptor by scint...	-
Peroxisome proliferator-activated receptor gamma	Kd	=	2000.0	nM	5.7	Binding affinity to PPARgamma	22260081
Nuclear receptor subfamily 1 group I member 2	EC50	=	2500.0	nM	5.6	Competitive binding affinity to human PXR LBD (111 to 434) by TR-FRET assay	20966043
Free fatty acid receptor 4	EC50	=	2600.0	nM	5.58	Agonist activity at human GPR120-G-alpha-16 fusion protein expressed in Flp-in H...	19007110
Free fatty acid receptor 1	EC50	=	2884.03	nM	5.54	Agonist activity at FFAR1 expressed in HEK 293 cells assessed as beta-arrestin r...	22519963
Free fatty acid receptor 1	EC50	=	3000.0	nM	5.52	Agonist activity at human FFA1 receptor expressed in human 1321N1 cells measured...	26928019
Free fatty acid receptor 1	EC50	=	3162.28	nM	5.5	Agonist activity at human FFA1 receptor expressed in human 1321N1 cells measured...	26928019
Free fatty acid receptor 4	EC50	=	3235.94	nM	5.49	Agonist activity at GPR120 expressed in HEK 293 cells assessed as beta-arrestin ...	22519963
Prostaglandin G/H synthase 1	Ki	=	4000.0	nM	5.4	Inhibition of COX-1 (unknown origin) using arachidonic acid as substrate assesse...	24088053
Free fatty acid receptor 1	EC50	=	5200.0	nM	5.28	Agonist activity at human GPR40 expressed in T-REx HEK293 cells assessed as effe...	19007110
Peroxisome proliferator-activated receptor gamma	IC50	=	6000.0	nM	5.22	Displacement of [3H]BRL49653 from Homo sapiens (human) PPARgamma receptor by sci...	-
Free fatty acid receptor 1	EC50	=	11090.0	nM	4.96	Agonist activity at recombinant human GPR40 expressed in HEK293 cells assessed a...	30212763
Prostaglandin G/H synthase 2	IC50	=	12000.0	nM	4.92	Inhibition of sheep COX2-mediated prostaglandin biosynthesis using [1-14C]arachi...	11421736
Cysteine protease ATG4B	IC50	=	15300.0	nM	4.82	PUBCHEM_BIOASSAY: Dose response confirmation of the uHTS fluorescent assay for i...	-
Peroxisome proliferator-activated receptor delta	IC50	=	16000.0	nM	4.8	Displacement of [3H]GW2433 from Homo sapiens (human) PPARdelta receptor by scint...	-
Unchecked	IC50	=	19000.0	nM	4.72	Inhibition of amidolytic activity of human recombinant soluble tissue factor/hum...	9834151
Phospholipase A2	IC50	=	22300.0	nM	4.65	PUBCHEM_BIOASSAY: Dose response counterscreen of uHTS hits for ATG4B inhibitors ...	-

Literature References

PubMed	DOI	Target Context	# Activities
33329762	10.1021/acsmedchemlett.0c00375	Unchecked	9
35131536	10.1016/j.ejmech.2022.114157	BV-2	6
20966043	10.1124/dmd.110.035105	Nuclear receptor subfamily 1 group I member 2	6
18044832	10.1021/jf072548w	Coptotermes formosanus	5
9834151	10.1021/np980117p	Unchecked	5
22459211	10.1016/j.bmc.2012.02.039	Unchecked	5
21903399	10.1016/j.bmc.2011.08.023	Unchecked	4
18044832	10.1021/jf072548w	Lactuca sativa	4
18044832	10.1021/jf072548w	Agrostis stolonifera	4
31678743	10.1016/j.ejmech.2019.111810	Staphylococcus aureus	3
21903399	10.1016/j.bmc.2011.08.023	RAW264.7	3
19007110	10.1021/jm800970b	Free fatty acid receptor 1	3
37468498	10.1038/s41467-023-40064-9	Nuclear receptor subfamily 1 group I member 2	3
16643058	10.1021/np050513p	Aromatase	3
37468498	10.1038/s41467-023-40064-9	Histamine H1 receptor	3
21903399	10.1016/j.bmc.2011.08.023	DNA polymerase lambda	2
26928019	10.1021/acs.jmedchem.5b01962	Free fatty acid receptor 1	2
24088053	10.1021/jm400813y	Prostaglandin G/H synthase 1	2
19007110	10.1021/jm800970b	Free fatty acid receptor 4	2
37468498	10.1038/s41467-023-40064-9	Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2	2

Data from ChEMBL 36 via Core Engine