2-{2-[2-(2-{6-amino-2-[2-(6-amino-2-{[1-(2-{2-[2-(2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido}-5-carbamimidamidopentanamido)-5-carbamimidamidopentanamido]-3-methylpentanamido}-5-carbamimidamidopentanoyl)pyrrolidin-2-yl]formamido}hexanamido)-4-methylpentanamido]hexanamido}-3-(1H-indol-3-yl)propanamido)-3-carboxypropanamido]-3-carbamoylpropanamido}-4-carbamoylbutanoic acid

• ChemBase ID: 103764
• Molecular Formular: C99H155N31O23
• Molecular Mass: 2147.4839
• Monoisotopic Mass: 2146.19121038
• SMILES: CCC(C)C(NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(N)Cc1ccc(O)cc1)C(=O)NC(CCCNC(=N)N)C(=O)N1CCCC1C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CCCCN)C(=O)NC(Cc1c[nH]c2c1cccc2)C(=O)NC(CC(=O)O)C(=O)NC(CC(=O)N)C(=O)NC(CCC(=O)N)C(=O)O
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)CCC(=O)N)CC(=O)N)CC(=O)O)Cc1c[nH]c2c1cccc2)CCCCN)CC(C)C)NC(=O)C1CCCN1C(=O)C(NC(=O)C(C(CC)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(Cc1ccc(cc1)O)N)CC(C)C)CCCNC(=N)N)CCCNC(=N)N)CCCNC(=N)N
• InChI: InChI=1S/C99H155N31O23/c1-7-55(6)81(129-86(142)66(28-18-40-112-98(107)108)118-83(139)65(27-17-39-111-97(105)106)120-88(144)70(44-54(4)5)125-89(145)71(46-56-21-9-8-10-22-56)117-79(135)52-115-78(134)51-116-82(138)61(102)45-57-31-33-59(131)34-32-57)94(150)122-67(29-19-41-113-99(109)110)95(151)130-42-20-30-75(130)93(149)121-64(26-14-16-38-101)85(141)124-69(43-53(2)3)87(143)119-63(25-13-15-37-100)84(140)126-72(47-58-50-114-62-24-12-11-23-60(58)62)90(146)128-74(49-80(136)137)92(148)127-73(48-77(104)133)91(147)123-68(96(152)153)35-36-76(103)132/h8-12,21-24,31-34,50,53-55,61,63-75,81,114,131H,7,13-20,25-30,35-49,51-52,100-102H2,1-6H3,(H2,103,132)(H2,104,133)(H,115,134)(H,116,138)(H,117,135)(H,118,139)(H,119,143)(H,120,144)(H,121,149)(H,122,150)(H,123,147)(H,124,141)(H,125,145)(H,126,140)(H,127,148)(H,128,146)(H,129,142)(H,136,137)(H,152,153)(H4,105,106,111)(H4,107,108,112)(H4,109,110,113)
• InChIKey: JMNJYGMAUMANNW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[2-(2-{6-amino-2-[2-(6-amino-2-{[1-(2-{2-[2-(2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido}-5-carbamimidamidopentanamido)-5-carbamimidamidopentanamido]-3-methylpentanamido}-5-carbamimidamidopentanoyl)pyrrolidin-2-yl]formamido}hexanamido)-4-methylpentanamido]hexanamido}-3-(1H-indol-3-yl)propanamido)-3-carboxypropanamido]-3-carbamoylpropanamido}-4-carbamoylbutanoic acid
• IUPAC Traditional name: 2-{2-[2-(2-{6-amino-2-[2-(6-amino-2-{[1-(2-{2-[2-(2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido}-5-carbamimidamidopentanamido)-5-carbamimidamidopentanamido]-3-methylpentanamido}-5-carbamimidamidopentanoyl)pyrrolidin-2-yl]formamido}hexanamido)-4-methylpentanamido]hexanamido}-3-(1H-indol-3-yl)propanamido)-3-carboxypropanamido]-3-carbamoylpropanamido}-4-carbamoylbutanoic acid
• Synonyms: Prodynorphin 209-225; Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Ile-Arg-Pro-Lys-Leu-Lys-Trp-Asp-Asn-Gln; DYNORPHIN A

Database IDs

• CAS Number: 80448-90-4
• PubChem SID: 162091492
• PubChem CID: 16129685

CALCULATED PROPERTIES

• Acid pKa: 3.0678174
• H Acceptors: 35
• H Donor: 33
• LogD (pH = 5.5): -21.601059
• LogD (pH = 7.4): -19.070448
• Log P: -11.4538555
• Molar Refractivity: 585.2326 cm^3
• Polarizability: 216.91753 Å^3
• Polar Surface Area: 917.37 Å^2
• Rotatable Bonds: 71
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

DETAILS

MP Biomedicals - 02152778

Source/Species: Porcine

REFERENCES

• Goldstein, A., et al., Proc. Natl. Acad. Sci. USA, 78: 7219 (1981).
• Tachibana, S., et al., Nature, 295: 339 (1982).