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158563-45-2

158563-45-2 structure
158563-45-2 structure
  • Name: (Met5,Pro6,D-Phe7,D-Trp9,Phe10)-α-MSH (5-13)
  • Chemical Name: (2S)-1-[(2S)-6-amino-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-2-amino-4-methylsulfanyl-butanoyl]pyrrolidine-2-carbonyl]amino]-3-phenyl-propanoyl]amino]-5-guanidino-pentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenyl-propanoyl]amino]hexanoyl]-N-[(1S)-1-carbamoyl-2-methyl-propyl]pyrrolidine-2-carboxamide
  • CAS Number: 158563-45-2
  • Molecular Formula: C61H87N15O9S
  • Molecular Weight: 1206.504
  • Catalog: Research Areas Cancer
  • Create Date: 2018-08-04 18:26:48
  • Modify Date: 2025-08-21 10:51:57
  • Nonapeptide-1 (Melanostatine-5), a peptide hormone, is a selective antagonist of MC1R (Ki: 40 nM). Nonapeptide-1 is a competitive α-MSH antagonist that potently inhibits intracellular cAMP and melanosome dispersion induced by α-MSH in melanocytes (IC50: 2.5 nM and 11 nM, respectively). Nonapeptide-1 inhibits melanin synthesis, and can be used in the research of skin pigmentation and regulation of steroid production in the adrenal gland, skin cancer[1][2][3].
Name (2S)-1-[(2S)-6-amino-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-2-amino-4-methylsulfanyl-butanoyl]pyrrolidine-2-carbonyl]amino]-3-phenyl-propanoyl]amino]-5-guanidino-pentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenyl-propanoyl]amino]hexanoyl]-N-[(1S)-1-carbamoyl-2-methyl-propyl]pyrrolidine-2-carboxamide
Synonyms (S)-1-(L-methionyl)-N-((R)-1-(((S)-1-(((R)-1-(((S)-1-(((S)-6-amino-1-((S)-2-(((S)-1-amino-3-methyl-1-oxobutan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-oxohexan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)amino)-5-guanidino-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)pyrrolidine-2-carboxamide
Nonapeptide-1
Melitane
H-Met-Pro-D-Phe-Arg-D-Trp-Phe-Lys-Pro-Val-NH2
L-Methionyl-L-prolyl-D-phenylalanyl-L-arginyl-D-tryptophyl-L-phenylalanyl-L-lysyl-L-prolyl-L-valinamide
Melanostatine
Description Nonapeptide-1 (Melanostatine-5), a peptide hormone, is a selective antagonist of MC1R (Ki: 40 nM). Nonapeptide-1 is a competitive α-MSH antagonist that potently inhibits intracellular cAMP and melanosome dispersion induced by α-MSH in melanocytes (IC50: 2.5 nM and 11 nM, respectively). Nonapeptide-1 inhibits melanin synthesis, and can be used in the research of skin pigmentation and regulation of steroid production in the adrenal gland, skin cancer[1][2][3].
Related Catalog
Target

MC1R:40 nM (Ki)

MC3R:0.47 μM (Ki)

MC4R:1.34 μM (Ki)

MC5R:2.4 μM (Ki)

In Vitro Nonapeptide-1 (153N-6) inhibits α-melanocyte hormone (α-MSH)-induced melanosome dispersion, with an IC50 value of 11 nM[1]. Nonapeptide-1 (0.1 nM-1 μΜ, 30 min) inhibits α-MSH-induced intracellular cAMP levels in melanocytes, with an IC50 of 2.5 nM[1]. Nonapeptide-1 (153N-6) shows highest affinity for MC1R (Ki: 40 nM) in COS-1 cells expressing human receptors, and is selective for MC1R over MC3R, MC4R, and MC5R (Ki: 0.47, 1.34, and 2.4 μΜ, respectively)[2]. Nonapeptide-1 (N-1A, 20 μΜ, 3 days) inhibits the basal melanin synthesis and reverses UVA-induced melanin increase in Human epidermal melanocytes (HEM cells) and HaCaT cells[3]. Nonapeptide-1 (20 μΜ, 3 days) competes with α-MSH and downregulates the expression of MC1R, tyrosinase, TRP1, TRP2, and MITF via binding to MC1R in HaCaT cells and HEM cells[3]. Western Blot Analysis[3] Cell Line: HaCaT cells, Human epidermal melanocytes (HEM) Concentration: 20 μΜ Incubation Time: 3 days Result: Downregulated the expression of MC1R, tyrosinase, TRP1, TRP2, and MITF.
References

[1]. Jayawickreme CK, et al. Discovery and structure-function analysis of alpha-melanocyte-stimulating hormone antagonists. J Biol Chem. 1994 Nov 25;269(47):29846-54.

[2]. Schiöth, H.B., et al. Characterization of the binding of MSH-B, HB-228, GHRP-6 and 153N-6 to the human melanocortin receptor subtypes. Neuropeptides 31(6), 565-571 (1997).

[3]. Jiaoquan Chen, et al. Effects of tea polyphenols on UVA-induced melanogenesis via inhibition of α-MSH-MC1R signalling pathway. Postepy Dermatol Alergol. 2022 Apr;39(2):327-335.

Density 1.4±0.1 g/cm3
Molecular Formula C61H87N15O9S
Molecular Weight 1206.504
Exact Mass 1205.653198
PSA 413.34000
LogP 3.90
Index of Refraction 1.672
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