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

• ChemBase ID: 153750
• Molecular Formular: C89H139N27O24S4
• Molecular Mass: 2099.48246
• Monoisotopic Mass: 2097.93691246
• SMILES: C[C@H]([C@@H](C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC1=O)CCSC)C(C)C)CCCNC(=N)N)C(C)C)Cc1ccc(cc1)O)CCCNC(=N)N)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](C(C)C)C(=O)O)NC(=O)[C@H](CC(=O)O)N)O
• 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)C(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)O)Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@H](CC(=O)O)N)CCSC)CCCNC(=N)N
• InChI: InChI=1S/C89H139N27O24S4/c1-43(2)67-82(135)101-40-64(119)102-53(18-12-30-97-87(91)92)74(127)113-68(44(3)4)83(136)109-59(36-47-22-24-49(118)25-23-47)77(130)107-58(20-14-32-99-89(95)96)85(138)116-33-15-21-63(116)81(134)111-62(80(133)108-60(37-48-39-100-52-17-11-10-16-50(48)52)78(131)104-55(26-27-65(120)121)75(128)114-69(45(5)6)86(139)140)42-144-143-41-61(79(132)105-57(29-35-142-9)76(129)112-67)110-72(125)54(19-13-31-98-88(93)94)103-73(126)56(28-34-141-8)106-84(137)70(46(7)117)115-71(124)51(90)38-66(122)123/h10-11,16-17,22-25,39,43-46,51,53-63,67-70,100,117-118H,12-15,18-21,26-38,40-42,90H2,1-9H3,(H,101,135)(H,102,119)(H,103,126)(H,104,131)(H,105,132)(H,106,137)(H,107,130)(H,108,133)(H,109,136)(H,110,125)(H,111,134)(H,112,129)(H,113,127)(H,114,128)(H,115,124)(H,120,121)(H,122,123)(H,139,140)(H4,91,92,97)(H4,93,94,98)(H4,95,96,99)/t46-,51+,53+,54+,55+,56+,57+,58+,59+,60+,61+,62+,63+,67+,68+,69+,70+/m1/s1
• InChIKey: ORRDHOMWDPJSNL-KHBOZDSRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-2-{[(3R,8R,11S,14S,20S,23S,26S,29S,34aS)-8-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-amino-3-carboxypropanamido]-3-hydroxybutanamido]-4-(methylsulfanyl)butanamido]-5-carbamimidamidopentanamido]-20,29-bis(3-carbamimidamidopropyl)-26-[(4-hydroxyphenyl)methyl]-11-[2-(methylsulfanyl)ethyl]-1,9,12,15,18,21,24,27,30-nonaoxo-14,23-bis(propan-2-yl)-dotriacontahydropyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20,23,26,29-nonaazacyclodotriacontan-3-yl]formamido}-3-(1H-indol-3-yl)propanamido]-4-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S)-2-{[(3R,8R,11S,14S,20S,23S,26S,29S,34aS)-8-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-amino-3-carboxypropanamido]-3-hydroxybutanamido]-4-(methylsulfanyl)butanamido]-5-carbamimidamidopentanamido]-20,29-bis(3-carbamimidamidopropyl)-26-[(4-hydroxyphenyl)methyl]-14,23-diisopropyl-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-3-yl]formamido}-3-(1H-indol-3-yl)propanamido]-4-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}butanoic acid
• Synonyms: Melanin Concentrating Hormone salmon

Database IDs

• CAS Number: 87218-84-6
• MDL Number: MFCD00080194
• PubChem SID: 162247889
• PubChem CID: 16167455

CALCULATED PROPERTIES

• Acid pKa: 2.9489312
• H Acceptors: 34
• H Donor: 31
• LogD (pH = 5.5): -14.456763
• LogD (pH = 7.4): -12.779103
• Log P: -12.0791025
• Molar Refractivity: 560.8634 cm^3
• Polarizability: 207.34277 Å^3
• Polar Surface Area: 836.68 Å^2
• Rotatable Bonds: 46
• 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

Product Information

• Purity: ≥90%
• Empirical Formula (Hill Notation): C89H139N27O24S4

DETAILS

Sigma Aldrich - M8441

Amino Acid Sequence
Asp-Thr-Met-Arg-Cys-Met-Val-Gly-Arg-Val-Tyr-Arg-Pro-Cys-Trp-Glu-Val [Disulfide bridge: 5-14]
Application
Hypothalamic appetite stimulant; ligand for somatostatin-like receptor 1 (SLC-1).