4-[(5-amino-1-{[1-({3-carbamoyl-1-[(1-{2-[(1-{[1-({1-[(1-carboxy-3-methylbutyl)carbamoyl]-2-hydroxypropyl}carbamoyl)-2-methylpropyl]carbamoyl}-3-methylbutyl)carbamoyl]pyrrolidin-1-yl}-3-hydroxy-1-oxobutan-2-yl)carbamoyl]propyl}carbamoyl)-2-hydroxyethyl]carbamoyl}pentyl)carbamoyl]-4-[2-(2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}-3-hydroxybutanamido)-3-hydroxypropanamido]butanoic acid

• ChemBase ID: 105497
• Molecular Formular: C83H131N19O27S
• Molecular Mass: 1859.10434
• Monoisotopic Mass: 1857.91825103
• SMILES: CSCCC(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(N)Cc1ccc(O)cc1)C(=O)NC(C(C)O)C(=O)NC(CO)C(=O)NC(CCC(=O)O)C(=O)NC(CCCCN)C(=O)NC(CO)C(=O)NC(CCC(=O)N)C(=O)NC(C(C)O)C(=O)N1CCCC1C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(C(C)O)C(=O)NC(CC(C)C)C(=O)O
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)CC(C)C)C(O)C)C(C)C)CC(C)C)C(O)C)CCC(=O)N)CO)NC(=O)C(NC(=O)C(NC(=O)C(C(O)C)NC(=O)C(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(Cc1ccc(cc1)O)N)CCSC)CO)CCC(=O)O
• InChI: InChI=1S/C83H131N19O27S/c1-41(2)33-55(75(120)98-65(43(5)6)79(124)100-67(45(8)106)80(125)95-57(83(128)129)34-42(3)4)94-78(123)60-20-16-31-102(60)82(127)68(46(9)107)101-72(117)52(25-27-61(86)109)91-76(121)58(39-103)96-70(115)51(19-14-15-30-84)90-71(116)53(26-28-64(112)113)92-77(122)59(40-104)97-81(126)66(44(7)105)99-73(118)54(29-32-130-10)93-74(119)56(36-47-17-12-11-13-18-47)89-63(111)38-87-62(110)37-88-69(114)50(85)35-48-21-23-49(108)24-22-48/h11-13,17-18,21-24,41-46,50-60,65-68,103-108H,14-16,19-20,25-40,84-85H2,1-10H3,(H2,86,109)(H,87,110)(H,88,114)(H,89,111)(H,90,116)(H,91,121)(H,92,122)(H,93,119)(H,94,123)(H,95,125)(H,96,115)(H,97,126)(H,98,120)(H,99,118)(H,100,124)(H,101,117)(H,112,113)(H,128,129)
• InChIKey: GASYAMBJHBRTOE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(5-amino-1-{[1-({3-carbamoyl-1-[(1-{2-[(1-{[1-({1-[(1-carboxy-3-methylbutyl)carbamoyl]-2-hydroxypropyl}carbamoyl)-2-methylpropyl]carbamoyl}-3-methylbutyl)carbamoyl]pyrrolidin-1-yl}-3-hydroxy-1-oxobutan-2-yl)carbamoyl]propyl}carbamoyl)-2-hydroxyethyl]carbamoyl}pentyl)carbamoyl]-4-[2-(2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}-3-hydroxybutanamido)-3-hydroxypropanamido]butanoic acid
• IUPAC Traditional name: 4-[(5-amino-1-{[1-({3-carbamoyl-1-[(1-{2-[(1-{[1-({1-[(1-carboxy-3-methylbutyl)carbamoyl]-2-hydroxypropyl}carbamoyl)-2-methylpropyl]carbamoyl}-3-methylbutyl)carbamoyl]pyrrolidin-1-yl}-3-hydroxy-1-oxobutan-2-yl)carbamoyl]propyl}carbamoyl)-2-hydroxyethyl]carbamoyl}pentyl)carbamoyl]-4-[2-(2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}-3-hydroxybutanamido)-3-hydroxypropanamido]butanoic acid
• Synonyms: β-Lipotropin 61-77; Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu; γ-ENDORPHIN

Database IDs

• CAS Number: 60893-02-9
• PubChem SID: 162092644
• PubChem CID: 16161109

CALCULATED PROPERTIES

• Acid pKa: 3.1644104
• H Acceptors: 29
• H Donor: 26
• LogD (pH = 5.5): -13.127314
• LogD (pH = 7.4): -13.276816
• Log P: -13.127858
• Molar Refractivity: 462.2975 cm^3
• Polarizability: 182.04602 Å^3
• Polar Surface Area: 747.92 Å^2
• Rotatable Bonds: 59
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 0°C

REFERENCES

• Guillemin, R., C. & E. News , 18, Aug. 16, 1976.
• Ling, N., Biochem. Biophys. Res. Commun. , 74 : 248 (1977).
• Austen, B.M. and Smyth, D.G., Biochem. Biophys. Res. Commun. , 76 : 477 (1977).