LPA   Click here for help

GtoPdb Ligand ID: 2906

Synonyms: 1-oleoyl-LPA | lysophosphatidic acid
Compound class: Metabolite
Comment: LPA is small biogenic and endogenous phospholipid derivative in mammals which acts as a potent signaling molecule
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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 7
Hydrogen bond donors 3
Rotatable bonds 21
Topological polar surface area 123.1
Molecular weight 436.26
XLogP 5.9
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)O)O
Isomeric SMILES CCCCCCCC/C=C\CCCCCCCC(=O)OCC(COP(=O)(O)O)O
InChI InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-
InChI Key WRGQSWVCFNIUNZ-KTKRTIGZSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Natural/Endogenous Targets
Target
GPR87
P2RY10
LPA1 receptor
LPA2 receptor
LPA3 receptor
LPA4 receptor
LPA5 receptor
LPA6 receptor
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
LPA5 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 8.2 pKd - 8
⤷ pKd 8.2 (Kd 6.4x10-9 M) [8]
LPA4 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.3 pKd - 11
⤷ pKd 7.3 [11]
LPA4 receptor Ligand is endogenous in the given species Mm Agonist Agonist 7.3 pKd - 11
⤷ pKd 7.3 (Kd 4.5x10-8 M) [11]
LPA3 receptor Ligand is endogenous in the given species Hs Agonist Agonist 6.7 pKd - 2
⤷ pKd 6.7 [2]
LPA1 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 7.9 – 8.3 pEC50 - 4-5,7
⤷ pEC50 7.9 – 8.3 (EC50 1.17x10-8 – 5x10-9 M) [4-5,7]
LPA2 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 8.0 – 8.2 pEC50 - 1,7
⤷ pEC50 8.0 – 8.2 (EC50 1x10-8 – 6.8x10-9 M) [1,7]
GPR87 Ligand is endogenous in the given species Hs Agonist Agonist 7.4 pEC50 - 10,16
⤷ pEC50 7.4 [10,16]
LPA2 receptor Ligand is endogenous in the given species Hs Agonist Agonist 6.7 – 8.2 pEC50 - 6,14
⤷ pEC50 6.7 – 8.2 [6,14]
P2RY10 Ligand is endogenous in the given species Hs Agonist Agonist 6.9 pEC50 - 10
⤷ pEC50 6.9 [10]
LPA3 receptor Ligand is endogenous in the given species Mm Agonist Agonist 6.6 pEC50 - 7
⤷ pEC50 6.6 (EC50 2.53x10-7 M) [7]
LPA5 receptor Ligand is endogenous in the given species Hs Agonist Agonist 4.3 – 7.9 pEC50 - 9,12,15
⤷ pEC50 4.3 – 7.9 [9,12,15]
LPA6 receptor Ligand is endogenous in the given species Hs Agonist Agonist 6.0 pEC50 - 13,17
⤷ pEC50 6.0 [13,17]
LPA6 receptor Ligand is endogenous in the given species Mm Agonist Partial agonist 6.0 pEC50 - 17
⤷ pEC50 6.0 (EC50 1x10-6 M) [17]
Targets where the ligand is described in the comment field
Target Comment
autotaxin Autotaxin is an extracellular multifunctional enzyme. Its lysophospholipase D activity hydrolyzes lysophosphatidylcholine to form the bioactive lipid lysophosphatidic acid (LPA). Autotaxin is considered to be the main source of LPA in vivo. It also acts on other substrates to produce additional bioactive lipids, for example generating sphingosine-1-phosphate (S1P) from sphingosylphosphorylcholine [3].
Ligand mentioned in the following text fields
1C. Peroxisome proliferator-activated receptors overview
Lysophospholipid (LPA) receptors overview
Phosphatidylcholine-specific phospholipase D comments