peptide 30 [PMID: 27019010]   Click here for help

GtoPdb Ligand ID: 9253

Immunopharmacology Ligand
Compound class: Peptide
Comment: Peptide 30 is a synthetic tetrapeptide reported to occupy the arachadonic acid binding site of cyclooxygenase 2 (COX-2) to bring about enzyme inhibition with an antiinflammatory/analgesic outcome [1]. Docking studies suggest that peptide 30 can occupy the active site of inducible nitric oxide synthase (iNOS; iNOS being well documented in pain mechanisms), although the COX-2 interaction is considered to be the major contributor to both the analgesic and antiinflammatory effects of the peptide in vivo.
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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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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 NCC(=O)NCC(=O)NC(C(=O)NC(C(=O)OC)CC(C)C)Cc1ccccc1
Isomeric SMILES NCC(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)OC)CC(C)C)Cc1ccccc1
InChI InChI=1S/C20H30N4O5/c1-13(2)9-16(20(28)29-3)24-19(27)15(10-14-7-5-4-6-8-14)23-18(26)12-22-17(25)11-21/h4-8,13,15-16H,9-12,21H2,1-3H3,(H,22,25)(H,23,26)(H,24,27)/t15-,16-/m0/s1
InChI Key CSHFHJNMIMPJST-HOTGVXAUSA-N
Bioactivity Comments
Peptide 30 is 100-fold selective for COX-2 over COX-1 [1].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
COX-2 Primary target of this compound Hs Inhibitor Inhibition 7.2 pIC50 - 1
⤷ pIC50 7.2 (IC50 6x10-8 M) [1]
COX-1 Hs Inhibitor Inhibition 5.2 pIC50 - 1
⤷ pIC50 5.2 (IC50 6x10-6 M) [1]