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 or derivative
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.

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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
References
1. Chignen Possi K, Mulumba M, Omri S, Garcia-Ramos Y, Tahiri H, Chemtob S, Ong H, Lubell WD. (2017)
Influences of Histidine-1 and Azaphenylalanine-4 on the Affinity, Anti-inflammatory, and Antiangiogenic Activities of Azapeptide Cluster of Differentiation 36 Receptor Modulators.
J Med Chem, 60 (22): 9263-9274. [PMID:29028172]
2. Proulx C, Picard É, Boeglin D, Pohankova P, Chemtob S, Ong H, Lubell WD. (2012)
Azapeptide analogues of the growth hormone releasing peptide 6 as cluster of differentiation 36 receptor ligands with reduced affinity for the growth hormone secretagogue receptor 1a.
J Med Chem, 55 (14): 6502-11. [PMID:22712585]
3. Turcotte S, Mellal K, Chingle R, Mulumba M, Omri S, Dif-Yaiche L, Chemtob S, Ong H, Lubell WD. (2018)
Azasulfurylpeptide Modulation of CD36-Mediated Inflammation Without Effect on Neovascularization.
Biomedicines, 6 (4). [PMID:30360354]