Compound Detail

CHEMBL15594

ARACHIDONIC ACID

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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL15594
Name	ARACHIDONIC ACID
Phase	Preclinical
Structure Type	MOL
InChI Key	YZXBAPSDXZZRGB-DOFZRALJSA-N

Known Names

Arachidonate Arachidonic acid Cis-5,8,11,14-eicosatetraenoic acid

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

304.5

MW (Da)

6.22

ALogP

HBA

HBD

37.3

PSA (Å²)

0.31

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C20H32O2
MW	304.47
Aromatic Rings	0
Heavy Atoms	22
NP-Likeness	1.06

Activity Summary

IC50 24 meas. best 8.33

EC50 3 meas. best 4.66

Kd 3 meas. best 6.75

Ki 2 meas. best 6.48

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
THP-1 CHEMBL614245	IC50	8.33	6.4933	4.7	3
Fatty acid-binding protein, adipocyte CHEMBL2083	Kd	6.75	6.75	180.0	1
Unchecked CHEMBL612545	IC50	6.52	5.46	300.0	2
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	Ki	6.48	6.48	330.0	1
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	IC50	6.22	6.22	602.6	1
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	Ki	6.09	6.09	820.0	1
Homo sapiens CHEMBL372	IC50	6.03	6.03	940.0	1
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	IC50	5.97	5.97	1071.5	1
Peroxisome proliferator-activated receptor alpha CHEMBL239	IC50	5.92	5.92	1200.0	2
Peroxisome proliferator-activated receptor gamma CHEMBL235	IC50	5.8	5.8	1600.0	1
Fatty acid-binding protein, adipocyte CHEMBL2083	IC50	5.56	5.425	2750.0	2
Peroxisome proliferator-activated receptor delta CHEMBL3979	IC50	5.51	5.51	3100.0	1
HSP60/HSP10 CHEMBL4106131	IC50	5.35	5.35	4500.0	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762	IC50	5.24	5.155	5800.0	2
GroEL/GroES CHEMBL4106139	IC50	5.14	4.945	7300.0	2
Hepatitis C virus CHEMBL379	IC50	5.0	4.61	10000.0	2
Hepatitis C virus CHEMBL379	EC50	4.66	4.66	22100.0	1
Aromatase CHEMBL1978	IC50	4.55	4.55	28200.0	1
Nuclear receptor subfamily 4 group A member 2 CHEMBL5002	Kd	4.3	4.3	50000.0	1
Serine/threonine-protein phosphatase 5 CHEMBL3425389	EC50	4.11	4.11	77590.0	2

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
THP-1	IC50	=	4.7	nM	8.33	Concentration required to inhibit production of LTC4 from THP-1 cells stimulated...	11229777
THP-1	IC50	=	180.0	nM	6.75	Concentration required to inhibit production of PGE-2 from THP-1 cells stimulate...	11229777
Fatty acid-binding protein, adipocyte	Kd	=	180.0	nM	6.75	Binding affinity against Adipocyte lipid binding protein	12036355
Unchecked	IC50	=	300.0	nM	6.52	Inhibition of mPGES1	18459759
Solute carrier organic anion transporter family member 1B1	Ki	=	330.0	nM	6.48	Ki values for sodium fluorescein (10 uM) uptake in OATP1B1-transfected CHO cells	23571415
Solute carrier organic anion transporter family member 1B1	IC50	=	602.56	nM	6.22	pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B1-transfected CHO ce...	23571415
Solute carrier organic anion transporter family member 1B3	Ki	=	820.0	nM	6.09	Ki values for sodium fluorescein (10 uM) uptake in OATP1B3-transfected CHO cells	23571415
Homo sapiens	IC50	=	940.0	nM	6.03	Concentration required to inhibit production of LTB4 from whole blood stimulated...	11229777
Solute carrier organic anion transporter family member 1B3	IC50	=	1071.52	nM	5.97	pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B3-transfected CHO ce...	23571415
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	IC50	=	1600.0	nM	5.8	Displacement of [3H]BRL49653 from Homo sapiens (human) PPARgamma receptor by sci...	-
Fatty acid-binding protein, adipocyte	IC50	=	2750.0	nM	5.56	Inhibition of FABP4 (unknown origin) incubated for 10 mins by fluorescence based...	35849941
Peroxisome proliferator-activated receptor delta	IC50	=	3100.0	nM	5.51	Displacement of [3H]GW2433 from Homo sapiens (human) PPARdelta receptor by scint...	-
HSP60/HSP10	IC50	=	4500.0	nM	5.35	Inhibition of human N-terminal octa-His-tagged HSP60 expressed in Escherichia co...	30852084
Fatty acid-binding protein, adipocyte	IC50	=	5130.0	nM	5.29	Inhibition of FABP4 (unknown origin)	28738306
Voltage-dependent L-type calcium channel subunit alpha-1C	IC50	=	5800.0	nM	5.24	Inhibition of L-type calcium channel measured using whole-cell patch clamp in ra...	22761000
GroEL/GroES	IC50	=	7300.0	nM	5.14	Inhibition of Escherichia coli GroEL expressed in Escherichia coliDH5alpha/Esche...	30852084
Voltage-dependent L-type calcium channel subunit alpha-1C	IC50	=	8500.0	nM	5.07	Inhibition of L-type calcium channel measured using whole-cell patch clamp in ra...	22761000
Hepatitis C virus	IC50	=	10000.0	nM	5.0	Inhibition of hepatitis C virus replication in Huh7-K2040 cells in presence of d...	18003907

Literature References

PubMed	DOI	Target Context	# Activities
18003907	10.1073/pnas.0708423104	Hepatitis C virus	12
15876534	10.1016/j.bmcl.2005.03.109	Oryctolagus cuniculus	7
18793849	10.1016/j.bmcl.2008.08.108	Unchecked	5
11229777	10.1016/s0960-894x(01)00003-8	Homo sapiens	5
30852084	10.1016/j.bmcl.2019.02.028	GroEL/GroES	4
31244108	10.1021/acs.jmedchem.9b00823	Prostaglandin G/H synthase 2	3
16643058	10.1021/np050513p	Aromatase	3
11229777	10.1016/s0960-894x(01)00003-8	THP-1	3
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B1	3
17954701	10.1128/aac.01009-07	Unchecked	3
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B3	3
12643906	10.1016/s0960-894x(03)00089-1	Unchecked	2
18459759	10.1021/jm800197b	Unchecked	2
22822908	10.1021/jm300673z	MDA-MB-468	2
30176215	10.1021/acs.jmedchem.8b00734	Transient receptor potential cation channel subfamily V member 2	2
37054560	10.1016/j.ejmech.2023.115350	Serine/threonine-protein phosphatase 5	2
22761000	10.1002/jat.2784	Voltage-dependent L-type calcium channel subunit alpha-1C	2
10328303	10.1016/s0960-894x(99)00148-1	Rattus norvegicus	2
9834151	10.1021/np980117p	Coagulation factor VII/tissue factor	1
12444669	10.1021/np020023m	Prostaglandin G/H synthase 2	1

Data from ChEMBL 36 via Core Engine