(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)-6-amino-2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-4-carboxybutanamido]acetyl}pyrrolidin-2-yl]formamido}-3-(4-hydroxyphenyl)propanamido]hexanamido]-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: 131691
• Molecular Formular: C98H138N26O29S
• Molecular Mass: 2176.36612
• Monoisotopic Mass: 2174.98437353
• SMILES: CSCC[C@@H](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)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)N
• Canonical SMILES: NCCCC[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)Cc1nc[nH]c1)CCC(=O)O)CCSC)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)N)CCC(=O)O)Cc1ccc(cc1)O
• InChI: InChI=1S/C98H138N26O29S/c1-154-40-33-66(115-85(140)61(19-7-9-34-99)112-91(146)68(42-54-25-27-57(126)28-26-54)120-93(148)73-22-12-37-122(73)77(128)50-108-83(138)64(29-31-78(129)130)111-82(137)59(101)45-80(133)134)89(144)114-65(30-32-79(131)132)88(143)119-70(44-56-48-104-52-109-56)92(147)117-67(41-53-15-3-2-4-16-53)90(145)113-63(21-11-36-105-98(102)103)86(141)118-69(43-55-47-106-60-18-6-5-17-58(55)60)84(139)107-49-76(127)110-72(51-125)95(150)124-39-14-24-75(124)96(151)123-38-13-23-74(123)94(149)116-62(20-8-10-35-100)87(142)121-71(97(152)153)46-81(135)136/h2-6,15-18,25-28,47-48,52,59,61-75,106,125-126H,7-14,19-24,29-46,49-51,99-101H2,1H3,(H,104,109)(H,107,139)(H,108,138)(H,110,127)(H,111,137)(H,112,146)(H,113,145)(H,114,144)(H,115,140)(H,116,149)(H,117,147)(H,118,141)(H,119,143)(H,120,148)(H,121,142)(H,129,130)(H,131,132)(H,133,134)(H,135,136)(H,152,153)(H4,102,103,105)/t59-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-/m0/s1
• InChIKey: KGWQRCLFOYBGIG-VOWYHKLBSA-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)-6-amino-2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-4-carboxybutanamido]acetyl}pyrrolidin-2-yl]formamido}-3-(4-hydroxyphenyl)propanamido]hexanamido]-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)-6-amino-2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-4-carboxybutanamido]acetyl}pyrrolidin-2-yl]formamido}-3-(4-hydroxyphenyl)propanamido]hexanamido]-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; β-Melanocyte Stimulating Hormone porcine

Database IDs

• CAS Number: 19941-13-0
• MDL Number: MFCD00133138
• PubChem SID: 162225968
• PubChem CID: 71308465

CALCULATED PROPERTIES

• Acid pKa: 2.771368
• H Acceptors: 36
• H Donor: 29
• LogD (pH = 5.5): -17.49631
• LogD (pH = 7.4): -20.971199
• Log P: -15.769534
• Molar Refractivity: 552.8872 cm^3
• Polarizability: 212.78795 Å^3
• Polar Surface Area: 879.72 Å^2
• Rotatable Bonds: 66
• 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: pig ... POMC(396863)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - M2018

Amino Acid Sequence
Asp-Glu-Gly-Pro-Tyr-Lys-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