compound 3c [PMID: 30360354]   Click here for help

GtoPdb Ligand ID: 10591

Synonyms: [As(4-F)F4]-GHRP-6 [2] | azasulfuryl-p-fluorophenylalanine-4-[As(4-F)F4]-GHRP-6 | H-His-D-Trp-Ala-(4-F)AsF-D-Phe-Lys-NH2 [2]
Immunopharmacology Ligand
Compound class: Peptide
Comment: Compound 3c acts as an antagonist of the scavenger receptor CD36 [3]. Structurally it is an azasulfurylpeptide derivative of the synthetic hexapeptide growth hormone releasing peptide-6 (GHRP-6) that has reported affinity for both CD36 and the ghrelin receptor (growth hormone secretagogue receptor).
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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.

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 NCCCCC(C(=O)N)NC(=O)C(NS(=O)(=O)N(NC(=O)C(NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(Cc1c[nH]cn1)N)C)CC1CCC(CC1)F)Cc1ccccc1
Isomeric SMILES NCCCC[C@@H](C(=O)N)NC(=O)[C@H](NS(=O)(=O)N(NC(=O)[C@@H](NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](Cc1c[nH]cn1)N)C)CC1CCC(CC1)F)Cc1ccccc1
InChI InChI=1S/C42H59FN12O7S/c1-26(50-41(59)36(20-29-22-48-34-12-6-5-11-32(29)34)52-40(58)33(45)21-31-23-47-25-49-31)39(57)53-55(24-28-14-16-30(43)17-15-28)63(61,62)54-37(19-27-9-3-2-4-10-27)42(60)51-35(38(46)56)13-7-8-18-44/h2-6,9-12,22-23,25-26,28,30,33,35-37,48,54H,7-8,13-21,24,44-45H2,1H3,(H2,46,56)(H,47,49)(H,50,59)(H,51,60)(H,52,58)(H,53,57)/t26-,28?,30?,33-,35-,36+,37+/m0/s1
InChI Key WYIBLRVRRGCPGV-FQYZGFJBSA-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/)
Bioactivity Comments
In vitro, compound 3c reduces CD36-mediated overproduction of NO, and pro-inflammatory chemokines and cytokines by macrophages stimulated by a TLR2 agonist (R-FSL-1) [3]. The anti-inflammatory effect of 3c is apparent in vivo, in a mouse model of induced retinal inflammation, but it has no anti-angiogenic effect in the mouse choroidal explant model.
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CD36 molecule (CD36 blood group) Rn Antagonist Antagonist 5.6 pIC50 - 2
⤷ pIC50 5.6 (IC50 2.53x10-6 M) [2]
Description: Measuring displacement of [125I]-Tyr-Bpa-Ala-hexarelin tracer from CD36 on purified membranes from rat heart in a radioligand binding assay.