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-5-yl)ethyl]carbamoyl}-4-(2-{2-[2-(2-amino-3-hydroxypropanamido)-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido}-4-(methylsulfanyl)butanamido)butanoic acid

• ChemBase ID: 155353
• Molecular Formular: C75H107N21O18S
• Molecular Mass: 1622.84698
• Monoisotopic Mass: 1621.78236669
• SMILES: CC(C)C(C(=O)N)NC(=O)C1CCCN1C(=O)C(CCCCN)NC(=O)CNC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(CCCNC(=N)N)NC(=O)C(Cc1ccccc1)NC(=O)C(Cc1cnc[nH]1)NC(=O)C(CCC(=O)O)NC(=O)C(CCSC)NC(=O)C(CO)NC(=O)C(Cc1ccc(cc1)O)NC(=O)C(CO)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(CO)N)Cc1ccc(cc1)O)CO)CCSC)CCC(=O)O)Cc1[nH]cnc1)Cc1ccccc1)CCCNC(=N)N
• InChI: InChI=1S/C75H107N21O18S/c1-41(2)62(63(78)103)95-73(113)59-19-12-29-96(59)74(114)53(17-9-10-27-76)86-60(100)37-84-65(105)56(33-44-35-83-49-16-8-7-15-47(44)49)92-66(106)50(18-11-28-82-75(79)80)87-69(109)55(31-42-13-5-4-6-14-42)91-71(111)57(34-45-36-81-40-85-45)93-67(107)51(24-25-61(101)102)88-68(108)52(26-30-115-3)89-72(112)58(39-98)94-70(110)54(90-64(104)48(77)38-97)32-43-20-22-46(99)23-21-43/h4-8,13-16,20-23,35-36,40-41,48,50-59,62,83,97-99H,9-12,17-19,24-34,37-39,76-77H2,1-3H3,(H2,78,103)(H,81,85)(H,84,105)(H,86,100)(H,87,109)(H,88,108)(H,89,112)(H,90,104)(H,91,111)(H,92,106)(H,93,107)(H,94,110)(H,95,113)(H,101,102)(H4,79,80,82)
• InChIKey: NMMSXFAQJQPZOI-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-5-yl)ethyl]carbamoyl}-4-(2-{2-[2-(2-amino-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-(3H-imidazol-4-yl)ethyl]carbamoyl}-4-(2-{2-[2-(2-amino-3-hydroxypropanamido)-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido}-4-(methylsulfanyl)butanamido)butanoic acid
• Synonyms: des-Ac-α-Melanocyte Stimulating Hormone

Database IDs

• CAS Number: 53697-27-1
• MDL Number: MFCD00133063
• PubChem SID: 24897236; 162249491
• PubChem CID: 16133042

CALCULATED PROPERTIES

• Acid pKa: 3.472819
• H Acceptors: 24
• H Donor: 23
• LogD (pH = 5.5): -13.285792
• LogD (pH = 7.4): -10.771627
• Log P: -8.7537
• Molar Refractivity: 428.2697 cm^3
• Polarizability: 163.66843 Å^3
• Polar Surface Area: 639.9 Å^2
• Rotatable Bonds: 49
• 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 ... F2R(2149), POMC(5443)

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C75H107N21O18S

DETAILS

Sigma Aldrich - M8267

Amino Acid Sequence
Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2
Biochem/physiol Actions
Retains ~10% of the activity of α-MSH.