PF-8380   Click here for help

GtoPdb Ligand ID: 9142

Synonyms: compound 21 [PMID: 26745766] | compound 4 [PMID: 23300119] | PF8380
PDB Ligand
Compound class: Synthetic organic
Comment: PF-8380 is reported as a novel autotaxin inhibitor [4] for use as a tool compound for investigating the in vivo role of autotaxin and LPA in inflammation and in cancer [2,4]. An ATX inhibitor compound named PF-8380 is claimed in patent WO2011151461 [1], but this has a different chemical structure from the entity we depict here and whch was disclosed in St-Coeur et al.'s primary publication [4].
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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 5
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 95.85
Molecular weight 477.09
XLogP 3.11
No. Lipinski's rules broken 0

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 Clc1cc(COC(=O)N2CCN(CC2)CCC(=O)c2ccc3c(c2)oc(=O)[nH]3)cc(c1)Cl
Isomeric SMILES Clc1cc(COC(=O)N2CCN(CC2)CCC(=O)c2ccc3c(c2)oc(=O)[nH]3)cc(c1)Cl
InChI InChI=1S/C22H21Cl2N3O5/c23-16-9-14(10-17(24)12-16)13-31-22(30)27-7-5-26(6-8-27)4-3-19(28)15-1-2-18-20(11-15)32-21(29)25-18/h1-2,9-12H,3-8,13H2,(H,25,29)
InChI Key JMSUDQYHPSNBSN-UHFFFAOYSA-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/)
Classification Click here for help
Compound class Synthetic organic
Synonyms Click here for help
compound 21 [PMID: 26745766] | compound 4 [PMID: 23300119] | PF8380
Database Links Click here for help
CAS Registry No. 1144035-53-9 (source: PubChem)
ChEMBL Ligand CHEMBL3186509
GtoPdb PubChem SID 315661227
PubChem CID 25265312
RCSB PDB Ligand 6ZO
Search Google for chemical match using the InChIKey JMSUDQYHPSNBSN-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JMSUDQYHPSNBSN
UniChem Compound Search for chemical match using the InChIKey JMSUDQYHPSNBSN-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JMSUDQYHPSNBSN-UHFFFAOYSA-N