4-{[1-({1-[(1-{[1-({[(6-amino-1-{2-[(1-carbamoyl-2-methylpropyl)carbamoyl]pyrrolidin-1-yl}-1-oxohexan-2-yl)carbamoyl]methyl}carbamoyl)-2-(1H-indol-3-yl)ethyl]carbamoyl}-4-carbamimidamidobutyl)carbamoyl]-2-phenylethyl}carbamoyl)-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-(2-{2-[2-(2-acetamido-3-hydroxypropanamido)-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido}-4-(methylsulfanyl)butanamido)butanoic acid

• ChemBase ID: 103387
• Molecular Formular: C77H109N21O19S
• Molecular Mass: 1664.88366
• Monoisotopic Mass: 1663.79293137
• SMILES: CSCCC(NC(=O)C(CO)NC(=O)C(Cc1ccc(O)cc1)NC(=O)C(CO)NC(=O)C)C(=O)NC(CCC(=O)O)C(=O)NC(Cc1c[nH]cn1)C(=O)NC(Cc1ccccc1)C(=O)NC(CCCNC(=N)N)C(=O)NC(Cc1c[nH]c2c1cccc2)C(=O)NCC(=O)NC(CCCCN)C(=O)N1CCCC1C(=O)NC(C(C)C)C(=O)N
• Canonical SMILES: NCCCCC(C(=O)N1CCCC1C(=O)NC(C(=O)N)C(C)C)NC(=O)CNC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C)CO)Cc1ccc(cc1)O)CO)CCSC)CCC(=O)O)Cc1nc[nH]c1)Cc1ccccc1)CCCNC(=N)N
• InChI: InChI=1S/C77H109N21O19S/c1-42(2)64(65(79)106)97-75(116)61-20-13-30-98(61)76(117)54(18-10-11-28-78)88-62(103)38-85-66(107)57(34-46-36-84-50-17-9-8-16-49(46)50)94-67(108)51(19-12-29-83-77(80)81)89-70(111)55(32-44-14-6-5-7-15-44)92-72(113)58(35-47-37-82-41-86-47)95-68(109)52(25-26-63(104)105)90-69(110)53(27-31-118-4)91-74(115)60(40-100)96-71(112)56(33-45-21-23-48(102)24-22-45)93-73(114)59(39-99)87-43(3)101/h5-9,14-17,21-24,36-37,41-42,51-61,64,84,99-100,102H,10-13,18-20,25-35,38-40,78H2,1-4H3,(H2,79,106)(H,82,86)(H,85,107)(H,87,101)(H,88,103)(H,89,111)(H,90,110)(H,91,115)(H,92,113)(H,93,114)(H,94,108)(H,95,109)(H,96,112)(H,97,116)(H,104,105)(H4,80,81,83)
• InChIKey: WHNFPRLDDSXQCL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[1-({1-[(1-{[1-({[(6-amino-1-{2-[(1-carbamoyl-2-methylpropyl)carbamoyl]pyrrolidin-1-yl}-1-oxohexan-2-yl)carbamoyl]methyl}carbamoyl)-2-(1H-indol-3-yl)ethyl]carbamoyl}-4-carbamimidamidobutyl)carbamoyl]-2-phenylethyl}carbamoyl)-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-(2-{2-[2-(2-acetamido-3-hydroxypropanamido)-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido}-4-(methylsulfanyl)butanamido)butanoic acid
• IUPAC Traditional name: 4-{[1-({1-[(1-{[1-({[(6-amino-1-{2-[(1-carbamoyl-2-methylpropyl)carbamoyl]pyrrolidin-1-yl}-1-oxohexan-2-yl)carbamoyl]methyl}carbamoyl)-2-(1H-indol-3-yl)ethyl]carbamoyl}-4-carbamimidamidobutyl)carbamoyl]-2-phenylethyl}carbamoyl)-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-(2-{2-[2-(2-acetamido-3-hydroxypropanamido)-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido}-4-(methylsulfanyl)butanamido)butanoic acid
• Synonyms: α-MSH; N-Acetyl-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH₂; α-MELANOCYTE STIMULATING HORMONE

Database IDs

• CAS Number: 581-05-5
• PubChem SID: 162090874
• PubChem CID: 16162729

CALCULATED PROPERTIES

• Acid pKa: 3.4907022
• H Acceptors: 24
• H Donor: 23
• LogD (pH = 5.5): -11.37419
• LogD (pH = 7.4): -10.220986
• Log P: -8.5977955
• Molar Refractivity: 437.1478 cm^3
• Polarizability: 167.07669 Å^3
• Polar Surface Area: 642.98 Å^2
• Rotatable Bonds: 50
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 0°C

REFERENCES

• Harris, J.J., et al., Nature, 179: 1346, (1957).
• Blake, J. and Li, C.H., Internatl. J. Protein Res., 111: 185, (1971).