arachidonic acid   Click here for help

GtoPdb Ligand ID: 2391

Synonyms: C20:4
PDB Ligand
Compound class: Metabolite
Comment: Arachidonic acid is a polyunsaturated fatty acid that demonstrates antibacterial activity against Staphylococcus aureus [2].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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 1.13.11.34 Arachidonic acid + O2 = LTA4 + H2O
12S-LOX 1.13.11.31, 1.13.11.31 Arachidonic acid + O2 => 12S-HPETE

Arachidonic acid + O2 => 12R-HPETE
15-LOX-1 1.13.11.33 Arachidonic acid + O2 = 15S-HPETE
COX-1 1.14.99.1, 1.14.99.1 Hydrogen donor + arachidonic acid + 2O2 = hydrogen acceptor + H2O + PGH2

Arachidonic acid => PGG2 => PGH2
15-LOX-2 1.13.11.33 Arachidonic acid + O2 = 15S-HPETE
12R-LOX 1.13.11.31, 1.13.11.31 Arachidonic acid + O2 => 12S-HPETE

Arachidonic acid + O2 => 12R-HPETE
COX-2 1.14.99.1, 1.14.99.1 Hydrogen donor + arachidonic acid + 2O2 = hydrogen acceptor + H2O + PGH2

Arachidonic acid => PGG2 => PGH2
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Fatty acid transport protein 1 21
Fatty acid transport protein 4 23
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
K2P13.1 Ligand is endogenous in the given species N/A Activator - - - 1x10-3 3
⤷ Conc range: 1x10-3 M studied at ~5 µM [3]
Kir3.4 Rn Activator Agonist - - 1x10-5 - 1x10-4 8
⤷ Conc range: 1x10-5 - 1x10-4 M [8]
Voltage: -80.0 mV
K2P4.1 Ligand is endogenous in the given species Rn Activator Positive - - 5x10-6 - 5x10-5 9
⤷ Conc range: 5x10-6 - 5x10-5 M [9]
TRPM2 Ligand is endogenous in the given species Hs Activator Potentiation - - 1x10-5 - 3x10-5 7
⤷ Conc range: 1x10-5 - 3x10-5 M [7]
Voltage: Physiological
Kir2.3 Ligand is endogenous in the given species Hs Activator Agonist 6.3 pEC50 - 11
⤷ pEC50 6.3 [11]
Voltage: -97.0 mV
TRPV4 Mm Activator Activation 5.0 pEC50 - 26
⤷ pEC50 5.0 [26]
K2P2.1 Ligand is endogenous in the given species Hs Activator Activation 5.0 pEC50 - 17
⤷ pEC50 5.0 (EC50 1x10-5 M) studied at 1-10 µM [17]
Kv4.2 Rn Channel blocker - 5.7 pIC50 - 24-25
⤷ pIC50 5.7 [24-25]
K2P3.1 Hs Channel blocker - 1.0 pIC50 - 12
⤷ pIC50 1.0 [12]
Voltage: 0.0 mV
TRPC6 Ligand is endogenous in the given species Hs Activator - - - -
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K2P4.1 Ligand is endogenous in the given species Hs Activator - - - - 6
⤷ studied at 1-10 µM [6]
K2P10.1 Ligand is endogenous in the given species Hs Activator - - - - 10
⤷ studied at 1-10 µM [10]
K2P18.1 Ligand is endogenous in the given species Hs Inhibitor - - - - 20
⤷ studied at 10-50 µM [20]
ClC-2 Ligand is endogenous in the given species Hs Activator - - - -
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Maxi Cl- Ligand is endogenous in the given species Hs Channel blocker (intracellular arachidonic acid) - - - -
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VRAC Ligand is endogenous in the given species Hs Channel blocker - - - -
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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 - - - 13
⤷ [13]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Endogenous substrates at Fatty acid transport protein 4 palmitic acid > oleic acid > butyric acid, γ-linolenic acid > arachidonic acid 23
Endogenous substrates at Fatty acid transport protein 1 arachidonic acid > palmitic acid > oleic acid > butyric acid 21
Rank order of potency at fatty acid binding protein 1 stearic acid, oleic acid > palmitic acid, linoleic acid > arachidonic acid, α-linolenic acid 18
Rank order of potency at fatty acid binding protein 2 stearic acid > palmitic acid,oleic acid > linoleic acid > arachidonic acid, α-linolenic acid 18
Rank order of potency at fatty acid binding protein 3 stearic acid, oleic acid, palmitic acid > linoleic acid, α-linolenic acid, arachidonic acid 18
Rank order of potency at fatty acid binding protein 4 oleic acid, palmitic acid, stearic acid, linoleic acid > α-linolenic acid, arachidonic acid 18
Rank order of potency at retinol binding protein 2 stearic acid > palmitic acid, oleic acid, linoleic acid, α-linolenic acid, arachidonic acid 19
Rank order of potency at cellular retinoic acid binding protein 1 tretinoin > alitretinoin
stearic acid > palmitic acid, oleic acid, linoleic acid, α-linolenic acid, arachidonic acid 		19
Targets where the ligand is described in the comment field
Target Comment
CYP2J2 Converts arachidonic acid to 14(R)-15(S)-epoxyeicosatrienoic acid [27]. Hydroxylates albendazole[28]. Expressed in cardiomyocytes [22].
CYP2C8 Converts arachidonic acid to 11(R)-12(S)-epoxyeicosatrienoic acid or 14(R)-15(S)-epoxyeicosatrienoic acid [29]. Drug substrates include amodiaquine and paclitaxel [1].
CYP4F22 Converts arachidonic acid to 16-HETE and 18-HETE [14]. Involved in production of acylceramide and skin barrier integrity [16]. Variants may influence ichthyosis [4-5,15].
Ligand mentioned in the following text fields
Cyclooxygenase overview
Eicosanoid turnover overview
Free fatty acid receptors overview
Lipoxygenases overview
Phospholipase A2 overview
Acid-sensing (proton-gated) ion channels (ASICs) comments
Glutamate transporter subfamily comments
Glycine transporter subfamily comments
Maxi chloride channel comments
Transient Receptor Potential channels (TRP) comments