3-{4-[(6-amino-1-{2-[(1-carbamoyl-2-methylpropyl)carbamoyl]pyrrolidin-1-yl}-1-oxohexan-2-yl)carbamoyl]-13-benzyl-10-(3-carbamimidamidopropyl)-22-acetamido-16-(1H-imidazol-5-ylmethyl)-7-(1H-indol-3-ylmethyl)-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-19-yl}propanoic acid

• ChemBase ID: 154645
• Molecular Formular: C61H86N18O13S2
• Molecular Mass: 1343.57834
• Monoisotopic Mass: 1342.6063169
• SMILES: CC(C)C(C(=O)N)NC(=O)C1CCCN1C(=O)C(CCCCN)NC(=O)C1CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)Cc1c[nH]c2c1cccc2)CCCNC(=N)N)Cc1ccccc1)Cc1cnc[nH]1)CCC(=O)O)NC(=O)C
• Canonical SMILES: NCCCCC(C(=O)N1CCCC1C(=O)NC(C(=O)N)C(C)C)NC(=O)C1CSSCC(NC(=O)C)C(=O)NC(CCC(=O)O)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)Cc1c[nH]c2c1cccc2)CCCNC(=N)N)Cc1ccccc1)Cc1[nH]cnc1
• InChI: InChI=1S/C61H86N18O13S2/c1-33(2)50(51(63)83)78-59(91)48-19-12-24-79(48)60(92)42(17-9-10-22-62)73-58(90)47-31-94-93-30-46(70-34(3)80)57(89)72-41(20-21-49(81)82)53(85)76-45(27-37-29-66-32-69-37)56(88)74-43(25-35-13-5-4-6-14-35)54(86)71-40(18-11-23-67-61(64)65)52(84)75-44(55(87)77-47)26-36-28-68-39-16-8-7-15-38(36)39/h4-8,13-16,28-29,32-33,40-48,50,68H,9-12,17-27,30-31,62H2,1-3H3,(H2,63,83)(H,66,69)(H,70,80)(H,71,86)(H,72,89)(H,73,90)(H,74,88)(H,75,84)(H,76,85)(H,77,87)(H,78,91)(H,81,82)(H4,64,65,67)
• InChIKey: YJLHIGSOJAOBEV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{4-[(6-amino-1-{2-[(1-carbamoyl-2-methylpropyl)carbamoyl]pyrrolidin-1-yl}-1-oxohexan-2-yl)carbamoyl]-13-benzyl-10-(3-carbamimidamidopropyl)-22-acetamido-16-(1H-imidazol-5-ylmethyl)-7-(1H-indol-3-ylmethyl)-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-19-yl}propanoic acid
• IUPAC Traditional name: 3-{4-[(6-amino-1-{2-[(1-carbamoyl-2-methylpropyl)carbamoyl]pyrrolidin-1-yl}-1-oxohexan-2-yl)carbamoyl]-13-benzyl-10-(3-carbamimidamidopropyl)-22-acetamido-16-(3H-imidazol-4-ylmethyl)-7-(1H-indol-3-ylmethyl)-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-19-yl}propanoic acid
• Synonyms: N-Acetyl-[Cys4,10, D-Phe7]-α-Melanocyte Stimulating Hormone Fragment 4-13

Database IDs

• CAS Number: 91050-39-4
• MDL Number: MFCD00133557
• PubChem SID: 162248783; 24897201
• PubChem CID: 25089443

CALCULATED PROPERTIES

• Acid pKa: -1.0092655
• H Acceptors: 18
• H Donor: 17
• LogD (pH = 5.5): -9.404141
• LogD (pH = 7.4): -8.515918
• Log P: -6.066874
• Molar Refractivity: 357.4164 cm^3
• Polarizability: 135.84895 Å^3
• Polar Surface Area: 494.99 Å^2
• Rotatable Bonds: 25
• 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)
• Compostion: Peptide content, ≥70%
• Empirical Formula (Hill Notation): C61H86N18O13S2

DETAILS

Sigma Aldrich - M7907

Amino Acid Sequence
Ac-Cys-Glu-His-Phe-Arg-Trp-Cys-Lys-Pro-Val-NH2 [Disulfide bridge: 4-10]
Biochem/physiol Actions
Cyclic MSH analog that is resistant to tryptic degradation; potent agonist with prolonged melanotropic activity in frog and lizard skin bioassays.