SHU9119   Click here for help

GtoPdb Ligand ID: 1325

Synonyms: (Ac-cyclo-[Nle4Asp5,D-Nal(2)7,Lys10]α-MSH-(4-10)-NH2) | SHU 9119 | SHU-9119
Comment: SHU9119 is a melanocortin MC3/MC4 receptor antagonist and MC5 receptor agonist. This ligand entry was updated in August 2023, to more fully render its stereochemistry.
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2D Structure
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Canonical SMILES CCCC[C@@H](C(=O)N[C@H]1CC(=O)NCCCC[C@@H](C(=O)N)NC(=O)[C@H](CC2=CNC3=C2C=CC=C3)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](CC4=CC5=C(C=CC=C5)C=C4)NC(=O)[C@H](CC6=CN=CN6)NC1=O)NC(=O)C
Isomeric SMILES C(C=1C=2C(NC1)=CC=CC2)[C@@H]3NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](CC4=CC5=C(C=C4)C=CC=C5)NC(=O)[C@H](CC6=CN=CN6)NC(=O)[C@@H](NC([C@H](CCCC)NC(C)=O)=O)CC(=O)NCCCC[C@@H](C(N)=O)NC3=O
InChI InChI=1S/C54H71N15O9/c1-3-4-15-40(63-31(2)70)48(73)69-45-27-46(71)59-21-10-9-17-39(47(55)72)64-51(76)43(25-35-28-61-38-16-8-7-14-37(35)38)67-49(74)41(18-11-22-60-54(56)57)65-50(75)42(24-32-19-20-33-12-5-6-13-34(33)23-32)66-52(77)44(68-53(45)78)26-36-29-58-30-62-36/h5-8,12-14,16,19-20,23,28-30,39-45,61H,3-4,9-11,15,17-18,21-22,24-27H2,1-2H3,(H2,55,72)(H,58,62)(H,59,71)(H,63,70)(H,64,76)(H,65,75)(H,66,77)(H,67,74)(H,68,78)(H,69,73)(H4,56,57,60)/t39-,40-,41-,42+,43-,44-,45-/m0/s1
1. Adan RA, Szklarczyk AW, Oosterom J, Brakkee JH, Nijenhuis WA, Schaaper WM, Meloen RH, Gispen WH. (1999)
Characterization of melanocortin receptor ligands on cloned brain melanocortin receptors and on grooming behavior in the rat.
Eur J Pharmacol, 378: 249-258. [PMID:10493100]
2. Hruby VJ, Lu D, Sharma SD, Castrucci AL, Kesterson RA, al-Obeidi FA, Hadley ME, Cone RD. (1995)
Cyclic lactam alpha-melanotropin analogues of Ac-Nle4-cyclo[Asp5, D-Phe7,Lys10] alpha-melanocyte-stimulating hormone-(4-10)-NH2 with bulky aromatic amino acids at position 7 show high antagonist potency and selectivity at specific melanocortin receptors.
J Med Chem, 38 (18): 3454-61. [PMID:7658432]
3. MacNeil DJ, Howard AD, Guan X, Fong TM, Nargund RP, Bednarek MA, Goulet MT, Weinberg DH, Strack AM, Marsh DJ et al.. (2002)
The role of melanocortins in body weight regulation: opportunities for the treatment of obesity.
Eur J Pharmacol, 440 (2-3): 141-57. [PMID:12007532]
4. Schiƶth HB, Muceniece R, Mutulis F, Bouifrouri AA, Mutule I, Wikberg JE. (1999)
Further pharmacological characterization of the selective melanocortin 4 receptor antagonist HS014: comparison with SHU9119.
Neuropeptides, 33 (3): 191-6. [PMID:10657491]