linoleic acid   Click here for help

GtoPdb Ligand ID: 1052

Synonyms: C18:2 | linoleate | linolic acid | telfairic acid
PDB Ligand
Compound class: Metabolite or derivative
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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
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 280.24
XLogP 7.87
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=CCCCCCCCC(=O)O
Isomeric SMILES CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
InChI InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
InChI Key OYHQOLUKZRVURQ-HZJYTTRNSA-N
Natural/Endogenous Targets
Target
FFA4 receptor
Hepatocyte nuclear factor-4-α
Peroxisome proliferator-activated receptor-γ
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
15-LOX-2 1.13.11.33 Linoleic acid + O2 => 13S-HPODE
15-LOX-1 1.13.11.33 Linoleic acid + O2 => 13S-HPODE
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
FFA4 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 5.9 pEC50 - 1
⤷ pEC50 5.9 [1]
FFA1 receptor Hs Agonist Full agonist 4.4 – 5.7 pEC50 - 2,4-5
⤷ pEC50 4.4 – 5.7 (EC50 3.98x10-5 – 1.99x10-6 M) [2,4-5]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Kv2.1 Hs Activator - 5.6 pEC50 - 7
⤷ pEC50 5.6 [7]
Kv2.1 Hs Channel blocker - 5.1 pIC50 - 7
⤷ pIC50 5.1 [7]
TRPM8 Hs Channel blocker - - - -
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K2P10.1 Hs Activator - - - - 6
⤷ [6]
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Peroxisome proliferator-activated receptor-γ Ligand is endogenous in the given species Hs Agonist Full agonist 5.3 pKd - 3,10
⤷ pKd 5.3 [3,10]
Hepatocyte nuclear factor-4-α Ligand is endogenous in the given species Hs Agonist Full agonist - - - 11
⤷ [11]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Rank order of potency at fatty acid binding protein 1 stearic acid, oleic acid > palmitic acid, linoleic acid > arachidonic acid, α-linolenic acid 8
Rank order of potency at fatty acid binding protein 2 stearic acid > palmitic acid,oleic acid > linoleic acid > arachidonic acid, α-linolenic acid 8
Rank order of potency at fatty acid binding protein 3 stearic acid, oleic acid, palmitic acid > linoleic acid, α-linolenic acid, arachidonic acid 8
Rank order of potency at fatty acid binding protein 4 oleic acid, palmitic acid, stearic acid, linoleic acid > α-linolenic acid, arachidonic acid 8
Rank order of potency at retinol binding protein 2 stearic acid > palmitic acid, oleic acid, linoleic acid, α-linolenic acid, arachidonic acid 9
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 		9
Ligand mentioned in the following text fields
Free fatty acid receptors overview