(2S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S)-1-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-aminopropanamido]-4-carboxybutanamido]hexanamido]hexanamido]-3-carboxypropanamido]-4-carboxybutanamido]acetyl}pyrrolidin-2-yl]formamido}-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanamido]-4-(methylsulfanyl)butanamido]-4-carboxybutanamido]-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-(1H-indol-3-yl)propanamido]acetamido}-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}hexanamido]butanedioic acid

• ChemBase ID: 134170
• Molecular Formular: C118H174N34O35S
• Molecular Mass: 2660.91596
• Monoisotopic Mass: 2659.26015444
• SMILES: C[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)NCC(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)O)C(=O)O)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N1CCC[C@H]1C(=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)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CC(=O)O)CCCCN)CO)Cc1c[nH]c2c1cccc2)CCCNC(=N)N)Cc1ccccc1)Cc1c[nH]cn1)CCC(=O)O)CCSC)CCCNC(=N)N)Cc1ccc(cc1)O)CCC(=O)O)CC(=O)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)C)CCC(=O)O)CCCCN
• InChI: InChI=1S/C118H174N34O35S/c1-63(122)97(167)135-77(36-39-93(159)160)105(175)137-71(23-8-11-42-119)100(170)136-72(24-9-12-43-120)102(172)147-84(55-95(163)164)111(181)140-76(35-38-92(157)158)98(168)132-60-91(156)150-47-16-28-87(150)112(182)148-81(52-65-31-33-68(154)34-32-65)109(179)138-74(26-14-45-128-117(123)124)101(171)142-79(41-50-188-2)107(177)141-78(37-40-94(161)162)106(176)146-83(54-67-58-127-62-133-67)110(180)144-80(51-64-19-4-3-5-20-64)108(178)139-75(27-15-46-129-118(125)126)103(173)145-82(53-66-57-130-70-22-7-6-21-69(66)70)99(169)131-59-90(155)134-86(61-153)114(184)152-49-18-30-89(152)115(185)151-48-17-29-88(151)113(183)143-73(25-10-13-44-121)104(174)149-85(116(186)187)56-96(165)166/h3-7,19-22,31-34,57-58,62-63,71-89,130,153-154H,8-18,23-30,35-56,59-61,119-122H2,1-2H3,(H,127,133)(H,131,169)(H,132,168)(H,134,155)(H,135,167)(H,136,170)(H,137,175)(H,138,179)(H,139,178)(H,140,181)(H,141,177)(H,142,171)(H,143,183)(H,144,180)(H,145,173)(H,146,176)(H,147,172)(H,148,182)(H,149,174)(H,157,158)(H,159,160)(H,161,162)(H,163,164)(H,165,166)(H,186,187)(H4,123,124,128)(H4,125,126,129)/t63-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-/m0/s1
• InChIKey: XLLJFSCSXTYVTN-UPWOUFKKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S)-1-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-aminopropanamido]-4-carboxybutanamido]hexanamido]hexanamido]-3-carboxypropanamido]-4-carboxybutanamido]acetyl}pyrrolidin-2-yl]formamido}-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanamido]-4-(methylsulfanyl)butanamido]-4-carboxybutanamido]-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-(1H-indol-3-yl)propanamido]acetamido}-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}hexanamido]butanedioic acid
• IUPAC Traditional name: (2S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S)-1-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-aminopropanamido]-4-carboxybutanamido]hexanamido]hexanamido]-3-carboxypropanamido]-4-carboxybutanamido]acetyl}pyrrolidin-2-yl]formamido}-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanamido]-4-(methylsulfanyl)butanamido]-4-carboxybutanamido]-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-(1H-indol-3-yl)propanamido]acetamido}-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}hexanamido]butanedioic acid
• Synonyms: β-MSH human; β-Melanotropin human; β-Melanocyte Stimulating Hormone human

Database IDs

• CAS Number: 17908-57-5
• MDL Number: MFCD00167548
• PubChem SID: 162228447
• PubChem CID: 16172929

CALCULATED PROPERTIES

• Acid pKa: 2.695832
• H Acceptors: 46
• H Donor: 38
• LogD (pH = 5.5): -21.79026
• LogD (pH = 7.4): -28.367989
• Log P: -16.514565
• Molar Refractivity: 683.6052 cm^3
• Polarizability: 259.72128 Å^3
• Polar Surface Area: 1121.34 Å^2
• Rotatable Bonds: 85
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... POMC(5443)

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - M6513

Amino Acid Sequence
Ala-Glu-Lys-Lys-Asp-Glu-Gly-Pro-Tyr-Arg-Met-Glu-His-Phe-Arg-Trp-Gly-Ser-Pro-Pro-Lys-Asp
Linkage
Derived from β-lipotropin (37-58)
Biochem/physiol Actions
Hormone that stimulates melanogenesis; facilitates learning and memory; affects inflammatory and immune responses and peripheral nerve regeneration