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
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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2D Structure
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SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Peptide or derivative
IUPAC Name Click here for help
(2S)-6-amino-2-[(2R)-2-({[(2S)-2-[(2R)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-(1H-indol-3-yl)propanamido]-N'-[(4-fluorocyclohexyl)methyl]propanehydrazido]sulfonyl}amino)-3-phenylpropanamido]hexanamide
Synonyms Click here for help
[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]
Database Links Click here for help
GtoPdb PubChem SID 404859038
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