arachidonic acid   Click here for help

GtoPdb Ligand ID: 2391

Synonyms: C20:4
PDB Ligand
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 14
Topological polar surface area 37.3
Molecular weight 304.24
XLogP 8.35
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCC=CCC=CCC=CCC=CCCCC(=O)O
Isomeric SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
InChI InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
InChI Key YZXBAPSDXZZRGB-DOFZRALJSA-N
Natural/Endogenous Targets
Target
ClC-2
Maxi Cl-
protein kinase C zeta
VRAC
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
5-LOX
12S-LOX
15-LOX-2
15-LOX-1
12R-LOX
COX-2
COX-1
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Fatty acid transport protein 1 20
Fatty acid transport protein 4 22
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
K2P13.1 Ligand is endogenous in the given species N/A Activator - - - 1x10-3 2
Conc range: 1x10-3 M studied at ~5 µM [2]
Kir3.4 Rn Activator Agonist - - 1x10-5 - 1x10-4 7
Conc range: 1x10-5 - 1x10-4 M [7]
Voltage: -80.0 mV
K2P4.1 Ligand is endogenous in the given species Rn Activator Positive - - 5x10-6 - 5x10-5 8
Conc range: 5x10-6 - 5x10-5 M [8]
TRPM2 Ligand is endogenous in the given species Hs Activator Potentiation - - 1x10-5 - 3x10-5 6
Conc range: 1x10-5 - 3x10-5 M [6]
Voltage: Physiological
Kir2.3 Ligand is endogenous in the given species Hs Activator Agonist 6.3 pEC50 - 10
pEC50 6.3 [10]
Voltage: -97.0 mV
TRPV4 Mm Activator Activation 5.0 pEC50 - 25
pEC50 5.0 [25]
K2P2.1 Ligand is endogenous in the given species Hs Activator Activation 5.0 pEC50 - 16
pEC50 5.0 (EC50 1x10-5 M) studied at 1-10 µM [16]
Kv4.2 Rn Channel blocker - 5.7 pIC50 - 23-24
pIC50 5.7 [23-24]
K2P3.1 Hs Channel blocker - 1.0 pIC50 - 11
pIC50 1.0 [11]
Voltage: 0.0 mV
TRPC6 Ligand is endogenous in the given species Hs Activator - - - -
K2P4.1 Ligand is endogenous in the given species Hs Activator - - - - 5
studied at 1-10 µM [5]
K2P10.1 Ligand is endogenous in the given species Hs Activator - - - - 9
studied at 1-10 µM [9]
K2P18.1 Ligand is endogenous in the given species Hs Inhibitor - - - - 19
studied at 10-50 µM [19]
ClC-2 Ligand is endogenous in the given species Hs Activator - - - -
Maxi Cl- Ligand is endogenous in the given species Hs Channel blocker (intracellular arachidonic acid) - - - -
VRAC Ligand is endogenous in the given species Hs Channel blocker - - - -
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
protein kinase C zeta Ligand is endogenous in the given species Hs Activator Activation - - - 12
[12]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Targets where the ligand is described in the comment field
Target Comment
Ligand mentioned in the following text fields