158563-45-2
Chemical Structure
Nonapeptide-1
Synonym(s): Melanostatine-5
- CAS No.: 158563-45-2
- Formula:C61H87N15O9S
- Molecular Weight:1206.50
IUPAC Name: (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
InChIKey: KNFLNGRLKALWRF-LDXSYGEZSA-N
SMILES: O=C(N1[C@@H](CCC1)C(N[C@H](C(N)=O)C(C)C)=O)[C@H](CCCCN)NC([C@H](CC2=CC=CC=C2)NC([C@H](NC([C@H](CCCNC(N)=N)NC([C@@H](CC3=CC=CC=C3)NC([C@H]4N(CCC4)C([C@@H](N)CCSC)=O)=O)=O)=O)CC5=CNC6=CC=CC=C56)=O)=O
Biological Activity: 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].
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Nonapeptide-1 | 98.74% | 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. | ||||||||||||||||||||
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- [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. [Content Brief]
- [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). [Content Brief]
- [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. [Content Brief]
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