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Afamelanotide

Afamelanotide is a first-in-class, synthetic, 13-amino acid peptide analogue of the endogenous alpha melanocyte-stimulating hormone (α-MSH). It differs structurally from its endogenous counterpart by only two amino acids - these structural differences improve biological efficacy by imparting a greater affinity for its target and a longer biological half-life.

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CAT No: R1512

CAS No: 75921-69-6

Synonyms/Alias: Melanotan I;Melanotan-1;75921-69-6;NDP-alpha-MSH;4-Nle-7-phe-alpha-msh;CUV1647;afamelanotida;CUV 1647;CUV-1647;QW68W3J66U;Melanotan-I;scenesse;(Nle4,D-Phe7)-alpha-MSH;[Nle4,D-Phe7]-alpha-MSH;AC-Ser-Tyr-Ser-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2;Msh, 4-nle-7-phe-alpha-;Afamelanotide [INN];alpha-Msh, nle(4)-phe(7)-;AFAMELANOTIDE [MI];Afamelanotide [USAN:INN];AFAMELANOTIDE [USAN];[Nle4,D-Phe7]--MSH;(nle4,d-phe7)-.alpha.-msh;AFAMELANOTIDE [WHO-DD];alpha-Melanotropin, 4-L-norleucine-7-D-phenylalanine-;SCHEMBL22463810;AFAMELANOTIDE [ORANGE BOOK];DA-48757;(Nle4,D-Phe7)-alpha-MSH trifluoroacetate salt;Afamelanotide; MT-I; [Nle4,D-Phe7]-alpha-MSH;EN300-18527915;.ALPHA.-MELANOTROPIN (SWINE), 4-L-NORLEUCINE-7-D-PHENYLALANINE-;N-acetyl-L-seryl-L-tyrosyl-L-seryl-L-norleucyl-L-alpha-glutamyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophylglycyl-L-lysyl-L-prolyl-L-valinamide;N-acteyl-L-Ser-L-Tyr-L-Ser-L-Nle-L-Glu-L-His-D-Phe-L-Arg-L-Trp-Gly-L-Lys-L-Pro-L-Val-NH2;

Chemical Name: (4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-5-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-6-amino-1-[(2S)-2-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxohexan-2-yl]amino]-2-oxoethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

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Specification Technical Data Publications Customer reviews and Q&A
M.F/FormulaC78H111N21O19
M.W/Mr.1646.8
SequenceOne Letter Code:SYSXEHFRWGKPV
Three Letter Code:Ac-Ser-Tyr-Ser-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2
ActivityAgonist
Biological ActivitySynthetic analog of α-MSH that is an agonist at melanocortin receptors (Ki values are 0.085, 0.4, 3.8 and 5.1 nM for MC1, MC3, MC4 and MC5 receptors respectively).
TargetMelanocyte-stimulating hormone receptor
Shipping ConditionRoom temperature in continental US; may vary elsewhere.
InChIInChI=1S/C78H111N21O19/c1-5-6-19-52(91-75(116)61(41-101)97-72(113)57(34-46-24-26-49(103)27-25-46)94-74(115)60(40-100)88-44(4)102)68(109)92-54(28-29-64(105)106)70(111)96-59(36-48-38-83-42-87-48)73(114)93-56(33-45-16-8-7-9-17-45)71(112)90-53(22-14-31-84-78(81)82)69(110)95-58(35-47-37-85-51-20-11-10-18-50(47)51)67(108)86-39-63(104)89-55(21-12-13-30-79)77(118)99-32-15-23-62(99)76(117)98-65(43(2)3)66(80)107/h7-11,16-18,20,24-27,37-38,42-43,52-62,65,85,100-101,103H,5-6,12-15,19,21-23,28-36,39-41,79H2,1-4H3,(H2,80,107)(H,83,87)(H,86,108)(H,88,102)(H,89,104)(H,90,112)(H,91,116)(H,92,109)(H,93,114)(H,94,115)(H,95,110)(H,96,111)(H,97,113)(H,98,117)(H,105,106)(H4,81,82,84)/t52-,53-,54-,55-,56+,57-,58-,59-,60-,61-,62-,65-/m0/s1
InChI KeyUAHFGYDRQSXQEB-LEBBXHLNSA-N
Canonical SMILESCCCCC(C(=O)NC(CCC(=O)O)C(=O)NC(CC1=CN=CN1)C(=O)NC(CC2=CC=CC=C2)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NCC(=O)NC(CCCCN)C(=O)N5CCCC5C(=O)NC(C(C)C)C(=O)N)NC(=O)C(CO)NC(=O)C(CC6=CC=C(C=C6)O)NC(=O)C(CO)NC(=O)C
Isomeric SMILESCCCC[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N5CCC[C@H]5C(=O)N[C@@H](C(C)C)C(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](CC6=CC=C(C=C6)O)NC(=O)[C@H](CO)NC(=O)C

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5. Cationic cell-penetrating peptides are potent furin inhibitors

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