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Basic Information

Molecular Structure:
CAS No.:	75921-69-6
Name:	Melanotan-1

Formula:	C₇₈H₁₁₁N₂₁O₁₉
Molecular Weight:	1646.87
Synonyms:	alpha-Msh, nle(4)-phe(7)-;alpha-Msh, norleucyl(4)-D-phenylalanyl(7)-;(Nle4,D-Phe7)-alpha-MSH;Afamelanotide;Msh, 4-norleucyl-7-phenylalanine-alpha-;(Nle4-D-Phe7)-alpha-Melanocyte-stimulating hormone;alpha-Melanotropin, 4-L-norleucine-7-D-phenylalanine-;
EINECS:	211-519-9
Density:	1.46 g/cm³
PSA:	642.98000
LogP:	3.12050

Synthetic route

: 29022-11-5
N-(fluoren-9-ylmethoxycarbonyl)glycine

: 68858-20-8
Fmoc-Val-OH

: 71989-31-6
Fmoc-Pro-OH

: 71989-33-8
Fmoc-Ser(tBu)-OH

: 104091-09-0, 136083-74-4, 121343-82-6
(S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid

: 71989-38-3
Fmoc-Tyr(tBu)-OH

: 105047-45-8
Fmoc-Lys-OH

: 86123-10-6
Fmoc-D-Phe-OH

: 109425-51-6
Fmoc-His(Trt)-OH

: 77284-32-3
Fmoc-(S)-2-aminohexanoic acid

: 143824-78-6
3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester

: Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

: 75921-69-6
NDP-MSH

Conditions

Conditions	Yield
Stage #1: Fmoc-Val-OH With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.5h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid; Fmoc-Tyr(tBu)-OH; Fmoc-Lys-OH; Fmoc-D-Phe-OH; Fmoc-His(Trt)-OH; Fmoc-(S)-2-aminohexanoic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;

Yield

Stage #1: Fmoc-Val-OH With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.5h;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid; Fmoc-Tyr(tBu)-OH; Fmoc-Lys-OH; Fmoc-D-Phe-OH; Fmoc-His(Trt)-OH; Fmoc-(S)-2-aminohexanoic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;

...Expand

: 75921-69-6
NDP-MSH

: [125I]2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate

: [125I][Nle4, D-Phe7, FIB-Lys11]α-MSH

Conditions

Conditions	Yield
With borate buffer In acetonitrile at 45℃; for 0.5h; pH=8;

: 75921-69-6
NDP-MSH

: [18F]2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate

: [18F][Nle4, D-Phe7, FIB-Lys11]α-MSH

Conditions

Conditions	Yield
With borate buffer In acetonitrile at 50℃; for 0.166667h; pH=8;

: 75921-69-6
NDP-MSH

: 2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate

: C85H113FIN21O20

Conditions

Conditions	Yield
With borate buffer In acetonitrile at 20℃; for 1.5h; pH=8.6;	0.18 mg

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Specification

1. Introduction of Melanotan-1
Melanotan-1 is one kind of white to off-white powder. The systematic name of this chemical is N-acetyl-L-seryl-L-tyrosyl-L-seryl-L-norleucyl-L-α-glutamyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophylglycyl-L-lysyl-L-prolyl-L-valinamide. Besides, Melanotan-1 belongs to Peptide;ImmunomodulatorsHormones;Melanocyte Stimulating Hormone (MSH)Peptides and Proteins;α-Melanocyte Stimulating Hormone (α-MSH)Peptides for Cell Biology;Cytokines Growth Factors and Hormones (Obesity);Ion Channel Modulating Peptides;Melanocyte Stimulating Hormones (MSH);Obesity Research;Peptides for Cell Biology;Pituitary Hormones. In addition, Melanotan-1 classification codes are: Affinity labels; Anticarcinogenic agents; Antineoplastic Agents; Indicators and Reagents; Protective Agents. What's more, it should be stored at -20°C.

2. Properties of Melanotan-1
Physical properties about Melanotan-1 are:
(1)# of Rule of 5 Violations: 3; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 40; (7)#H bond donors: 26; (8)#Freely Rotating Bonds: 54; (9)Polar Surface Area: 383.16 Å²; (10)Index of Refraction: 1.674; (11)Molar Refractivity: 422.68 cm³; (12)Molar Volume: 1126.1 cm³; (13)Polarizability: 167.56×10^-24cm³; (14)Surface Tension: 64.7 dyne/cm; (15)Density: 1.46 g/cm³.

3. Structure Descriptors of Melanotan-1
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N1[C@H](C(=O)N[C@H](C(=O)N)C(C)C)CCC1)CCCCN)Cc3c2ccccc2nc3)CCCNC(=[N@H])N)Cc4ccc cc4)Cc5ncnc5)CCC(=O)O)CCCC)CO)Cc6ccc(O)cc6)[C@@H](NC(=O)C)CO
(2)InChI: InChI=1/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
(3)InChIKey: UAHFGYDRQSXQEB-LEBBXHLNBN

4. Safety information of Melanotan-1
WGK Germany: 3

5. Uses of Melanotan-1
The Melanotan-1, known as Afamelanotide, is a synthetic analog of the naturally occurring melanocortin peptide hormone alpha-melanocyte stimulating hormone (α-MSH), and α-MSH has been shown to induce skin pigmentation through melanogenesis and thereby subsequently reduce sun (UV) damage to UV exposed skin in preliminary studies and clinical trials.