(4S)-4-[(2S)-2-{[(3R,8R,11S,14S,20S,23S,26S,29S,34aS)-8-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-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: 153137
• Molecular Formular: C99H153N29O26S5
• Molecular Mass: 2325.77782
• Monoisotopic Mass: 2324.01451116
• 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)NC(=O)CCCC[C@H]1[C@@H]2[C@H](CS1)NC(=O)N2)O
• Canonical SMILES: CSCC[C@@H](C(=O)N[C@H](C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@@H]2CCCN2C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](Cc2ccc(cc2)O)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)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)CCCNC(=N)N)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)CC(=O)O
• InChI: InChI=1S/C99H153N29O26S5/c1-48(2)75-91(148)110-44-72(132)111-57(20-14-34-106-96(100)101)82(139)124-76(49(3)4)92(149)119-63(40-52-26-28-54(130)29-27-52)85(142)117-62(22-16-36-108-98(104)105)94(151)128-37-17-23-69(128)90(147)121-68(89(146)118-64(41-53-43-109-56-19-11-10-18-55(53)56)86(143)114-59(30-31-73(133)134)83(140)125-77(50(5)6)95(152)153)47-159-158-46-67(88(145)115-61(33-39-156-9)84(141)123-75)120-80(137)58(21-15-35-107-97(102)103)113-81(138)60(32-38-155-8)116-93(150)78(51(7)129)126-87(144)65(42-74(135)136)112-71(131)25-13-12-24-70-79-66(45-157-70)122-99(154)127-79/h10-11,18-19,26-29,43,48-51,57-70,75-79,109,129-130H,12-17,20-25,30-42,44-47H2,1-9H3,(H,110,148)(H,111,132)(H,112,131)(H,113,138)(H,114,143)(H,115,145)(H,116,150)(H,117,142)(H,118,146)(H,119,149)(H,120,137)(H,121,147)(H,123,141)(H,124,139)(H,125,140)(H,126,144)(H,133,134)(H,135,136)(H,152,153)(H4,100,101,106)(H4,102,103,107)(H4,104,105,108)(H2,122,127,154)/t51-,57+,58+,59+,60+,61+,62+,63+,64+,65+,66+,67+,68+,69+,70+,75+,76+,77+,78+,79+/m1/s1
• InChIKey: FKLSNVGEODBRRJ-KJQIIMNASA-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-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-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-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}-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: MCH Biotinylated; Biotinyl-Melanin-Concentrating Hormone from salmon

Database IDs

• MDL Number: MFCD00168126
• PubChem SID: 162247277
• PubChem CID: 71311593

CALCULATED PROPERTIES

• Acid pKa: 3.0598142
• H Acceptors: 35
• H Donor: 33
• LogD (pH = 5.5): -11.546467
• LogD (pH = 7.4): -11.534204
• Log P: -11.532442
• Molar Refractivity: 617.7144 cm^3
• Polarizability: 229.46924 Å^3
• Polar Surface Area: 880.89 Å^2
• Rotatable Bonds: 52
• 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

• Empirical Formula (Hill Notation): C99H153N29O26S5

DETAILS

Sigma Aldrich - B3559

Amino Acid Sequence
Biotinyl-Asp-Thr-Met-Arg-Cys-Met-Val-Gly-Arg-Val-Tyr-Arg-Pro-Cys-Trp-Glu-Val-OH [Disulfide bridge: 5-14]
Biochem/physiol Actions
Originally isolated from salmon pituitary glands, also found in the mammalian CNS. In lower vertebrates, MCH alters pigmentation by inducing melanosome aggregation within melanocytes of teleost fish, whereas it causes melanosome dispersion in amphibians and reptiles.