CAS 158563-45-2|(Met5,Pro6,D-Phe7,D-Trp9,Phe10)-α-MSH (5-13)

Introduction：Basic information about CAS 158563-45-2|(Met5,Pro6,D-Phe7,D-Trp9,Phe10)-α-MSH (5-13), including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. BiologicalActivity
3. Chemical & Physical Properties
4. Synonyms

Common Name	(Met5,Pro6,D-Phe7,D-Trp9,Phe10)-α-MSH (5-13)
CAS Number	158563-45-2	Molecular Weight	1206.504
Density	1.4±0.1 g/cm3	Boiling Point	/
Molecular Formula	C₆₁H₈₇N₁₅O₉S	Melting Point	/
MSDS	/	Flash Point	/

Names

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
Synonym	More Synonyms

BiologicalActivity

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	Research Areas >>CancerResearch Areas >>EndocrinologyResearch Areas >>Metabolic DiseaseSignaling Pathways >>GPCR/G Protein >>Melanocortin Receptor
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.

Chemical & Physical Properties

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
InChIKey	KNFLNGRLKALWRF-LDXSYGEZSA-N
SMILES	CSCCC(N)C(=O)N1CCCC1C(=O)NC(Cc1ccccc1)C(=O)NC(CCCN=C(N)N)C(=O)NC(Cc1c[nH]c2ccccc12)C(=O)NC(Cc1ccccc1)C(=O)NC(CCCCN)C(=O)N1CCCC1C(=O)NC(C(N)=O)C(C)C

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

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