Acetyl-(D-Arg10,Cys11,D-Phe14,Cys17)-β-MSH (10-17) amide
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Acetyl-(D-Arg10,Cys11,D-Phe14,Cys17)-β-MSH (10-17) amide

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Acetyl-(D-Arg10,Cys11,D-Phe14,Cys17)-β-MSH (10-17) amide, a selective and highly potent β-MSH-derived melanocortin-4 receptor (MC-4R) agonist, has sub-nanomolar potency with the binding affinities of 0.55±0.06, 16.78±1.53, 56.79±4.66 and <500 nM for human MC-4R, MC-1R, MC-3R and MC-5R, respectively.

Category
Peptide Inhibitors
Catalog number
BAT-015348
CAS number
819048-44-7
Molecular Formula
C51H70N18O11S2
Molecular Weight
1175.36
Acetyl-(D-Arg10,Cys11,D-Phe14,Cys17)-β-MSH (10-17) amide
IUPAC Name
3-[(4R,7S,10S,13R,16S,19S,22R)-22-[[(2R)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-13-benzyl-4-carbamoyl-10-[3-(diaminomethylideneamino)propyl]-16-(1H-imidazol-5-ylmethyl)-7-(1H-indol-3-ylmethyl)-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexazacyclotricos-19-yl]propanoic acid
Synonyms
Ac-D-Arg-Cys-Glu-His-D-Phe-Arg-Trp-Cys-NH2 (Disulfide bridge: Cys2-Cys8); N-acetyl-D-arginyl-L-cysteinyl-L-alpha-glutamyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophyl-L-cysteinamide (2->8)-disulfide; 3-[(4R,7S,10S,13R,16S,19S,22R)-22-{[N2-Acetyl-N5-(diaminomethylene)-D-ornithyl]amino}-13-benzyl-4-carbamoyl-10-{3-[(diaminomethylene)amino]propyl}-16-(1H-imidazol-5-ylmethyl)-7-(1H-indol-3-ylmethyl)-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-19-yl]propanoic acid; L-Cysteinamide, N2-acetyl-D-arginyl-L-cysteinyl-L-α-glutamyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophyl-, cyclic (2→8)-disulfide
Appearance
White Lyophilized Powder
Purity
≥95%
Density
1.56±0.1 g/cm3
Sequence
Ac-RCEHFRWC-NH2 (Disulfide bridge: Cys2-Cys8)
Storage
Store at -20°C
Solubility
Soluble in Water
InChI
InChI=1S/C51H70N18O11S2/c1-27(70)62-33(13-7-17-58-50(53)54)43(74)69-40-25-82-81-24-39(42(52)73)68-47(78)37(20-29-22-60-32-12-6-5-11-31(29)32)66-44(75)34(14-8-18-59-51(55)56)63-46(77)36(19-28-9-3-2-4-10-28)65-48(79)38(21-30-23-57-26-61-30)67-45(76)35(64-49(40)80)15-16-41(71)72/h2-6,9-12,22-23,26,33-40,60H,7-8,13-21,24-25H2,1H3,(H2,52,73)(H,57,61)(H,62,70)(H,63,77)(H,64,80)(H,65,79)(H,66,75)(H,67,76)(H,68,78)(H,69,74)(H,71,72)(H4,53,54,58)(H4,55,56,59)/t33-,34+,35+,36-,37+,38+,39+,40+/m1/s1
InChI Key
UNXFCHHFXJFRRB-ZSTGMXRXSA-N
Canonical SMILES
CC(=O)NC(CCCN=C(N)N)C(=O)NC1CSSCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCC(=O)O)CC2=CN=CN2)CC3=CC=CC=C3)CCCN=C(N)N)CC4=CNC5=CC=CC=C54)C(=O)N
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