(3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(3R,8R,11S,14S,20S,23S,26S,29S,34aS)-20,29-bis(3-carbamimidamidopropyl)-3-{[(1S)-1-{[(1S)-3-carbamoyl-1-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}propyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-26-[(4-hydroxyphenyl)methyl]-14-(2-methylpropyl)-11-[2-(methylsulfanyl)ethyl]-1,9,12,15,18,21,24,27,30-nonaoxo-23-(propan-2-yl)-dotriacontahydropyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20,23,26,29-nonaazacyclodotriacontan-8-yl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-3-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-3-phenylpropanamido]propanoic acid

• ChemBase ID: 133833
• Molecular Formular: C105H160N30O26S4
• Molecular Mass: 2386.8393
• Monoisotopic Mass: 2385.10028939
• SMILES: CC(C)C[C@H]1C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N1)CCSC)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(=O)O)N)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](C(C)C)C(=O)O)CCCNC(=N)N)Cc1ccc(cc1)O)C(C)C)CCCNC(=N)N
• Canonical SMILES: CSCC[C@@H]1NC(=O)[C@H](CSSC[C@H](NC(=O)[C@@H]2CCCN2C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC1=O)CC(C)C)CCCNC(=N)N)C(C)C)Cc1ccc(cc1)O)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)C(C)C)CCC(=O)N)Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)N)Cc1ccccc1)CC(=O)O)CCSC)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/C105H160N30O26S4/c1-53(2)42-70-86(144)118-50-80(138)119-64(24-16-36-114-103(108)109)90(148)133-83(55(5)6)100(158)130-73(45-58-28-30-60(136)31-29-58)93(151)124-69(26-18-38-116-105(112)113)101(159)135-39-19-27-78(135)99(157)132-77(98(156)128-74(46-59-49-117-63-23-15-14-22-61(59)63)95(153)121-66(32-33-79(107)137)91(149)134-84(56(7)8)102(160)161)52-165-164-51-76(97(155)123-68(35-41-163-10)88(146)126-70)131-87(145)65(25-17-37-115-104(110)111)120-92(150)71(43-54(3)4)127-89(147)67(34-40-162-9)122-96(154)75(48-82(141)142)129-94(152)72(44-57-20-12-11-13-21-57)125-85(143)62(106)47-81(139)140/h11-15,20-23,28-31,49,53-56,62,64-78,83-84,117,136H,16-19,24-27,32-48,50-52,106H2,1-10H3,(H2,107,137)(H,118,144)(H,119,138)(H,120,150)(H,121,153)(H,122,154)(H,123,155)(H,124,151)(H,125,143)(H,126,146)(H,127,147)(H,128,156)(H,129,152)(H,130,158)(H,131,145)(H,132,157)(H,133,148)(H,134,149)(H,139,140)(H,141,142)(H,160,161)(H4,108,109,114)(H4,110,111,115)(H4,112,113,116)/t62-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,83-,84-/m0/s1
• InChIKey: MWLPXSMFEPHETN-QRXCLJFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(3R,8R,11S,14S,20S,23S,26S,29S,34aS)-20,29-bis(3-carbamimidamidopropyl)-3-{[(1S)-1-{[(1S)-3-carbamoyl-1-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}propyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-26-[(4-hydroxyphenyl)methyl]-14-(2-methylpropyl)-11-[2-(methylsulfanyl)ethyl]-1,9,12,15,18,21,24,27,30-nonaoxo-23-(propan-2-yl)-dotriacontahydropyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20,23,26,29-nonaazacyclodotriacontan-8-yl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-3-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-3-phenylpropanamido]propanoic acid
• IUPAC Traditional name: (3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(3R,8R,11S,14S,20S,23S,26S,29S,34aS)-20,29-bis(3-carbamimidamidopropyl)-3-{[(1S)-1-{[(1S)-3-carbamoyl-1-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}propyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-26-[(4-hydroxyphenyl)methyl]-23-isopropyl-14-(2-methylpropyl)-11-[2-(methylsulfanyl)ethyl]-1,9,12,15,18,21,24,27,30-nonaoxo-docosahydro-2H-pyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20,23,26,29-nonaazacyclodotriacontan-8-yl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-3-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-3-phenylpropanamido]propanoic acid
• Synonyms: MCH; Melanin Concentrating Hormone rat

Database IDs

• CAS Number: 128315-56-0
• MDL Number: MFCD00080193
• PubChem SID: 162228110
• PubChem CID: 24868207

CALCULATED PROPERTIES

• Acid pKa: 2.966927
• H Acceptors: 36
• H Donor: 33
• LogD (pH = 5.5): -13.068428
• LogD (pH = 7.4): -11.393507
• Log P: -10.693514
• Molar Refractivity: 640.3239 cm^3
• Polarizability: 238.32181 Å^3
• Polar Surface Area: 917.74 Å^2
• Rotatable Bonds: 56
• 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: rat ... Pmch(24659)

Product Information

• Purity: ≥90% (HPLC)
• Compostion: Peptide content, ≥70%

DETAILS

Sigma Aldrich - M4542

Amino Acid Sequence
Asp-Phe-Asp-Met-Leu-Arg-Cys-Met-Leu-Gly-Arg-Val-Tyr-Arg-Pro-Cys-Trp-Gln-Val [Disulfide Bridge: 7-16]
Biochem/physiol Actions
Hypothalamic appetite stimulant; ligand for somatostatin-like receptor 1.