(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido]-3-hydroxybutanamido]-3-hydroxypropanamido]-4-carboxybutanamido]hexanamido]-3-hydroxypropanamido]-4-carbamoylbutanamido]-3-hydroxybutanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanamido]-3-methylbutanamido]-3-hydroxybutanamido]-4-methylpentanoic acid

• ChemBase ID: 130521
• Molecular Formular: C83H131N19O27S
• Molecular Mass: 1859.10434
• Monoisotopic Mass: 1857.91825103
• SMILES: C[C@H]([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N)O
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CC(C)C)[C@H](O)C)C(C)C)CC(C)C)[C@H](O)C)CCC(=O)N)CO)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](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)/t44-,45-,46-,50+,51+,52+,53+,54+,55+,56+,57+,58+,59+,60+,65+,66+,67+,68+/m1/s1
• InChIKey: GASYAMBJHBRTOE-WHDBNHDESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido]-3-hydroxybutanamido]-3-hydroxypropanamido]-4-carboxybutanamido]hexanamido]-3-hydroxypropanamido]-4-carbamoylbutanamido]-3-hydroxybutanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanamido]-3-methylbutanamido]-3-hydroxybutanamido]-4-methylpentanoic acid
• IUPAC Traditional name: gamma-endorphin
• Synonyms: Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu; Gamma-endorphin

Database IDs

• PubChem SID: 162224800
• PubChem CID: 16138008
• Wikipedia Title: Gamma-endorphin

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