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]hexanoic acid

• ChemBase ID: 132895
• Molecular Formular: C75H126N24O15
• Molecular Mass: 1603.95474
• Monoisotopic Mass: 1602.98344945
• SMILES: CCC(C)C(C(=O)NC(CCCNC(=N)N)C(=O)N1CCCC1C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CCCCN)C(=O)O)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(Cc1ccc(cc1)O)N
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NC(C(=O)O)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/C75H126N24O15/c1-7-45(6)61(70(111)94-53(25-17-35-87-75(83)84)71(112)99-36-18-26-58(99)69(110)93-50(21-11-13-31-76)64(105)96-56(38-44(4)5)67(108)95-54(72(113)114)22-12-14-32-77)98-65(106)52(24-16-34-86-74(81)82)91-63(104)51(23-15-33-85-73(79)80)92-66(107)55(37-43(2)3)97-68(109)57(40-46-19-9-8-10-20-46)90-60(102)42-88-59(101)41-89-62(103)49(78)39-47-27-29-48(100)30-28-47/h8-10,19-20,27-30,43-45,49-58,61,100H,7,11-18,21-26,31-42,76-78H2,1-6H3,(H,88,101)(H,89,103)(H,90,102)(H,91,104)(H,92,107)(H,93,110)(H,94,111)(H,95,108)(H,96,105)(H,97,109)(H,98,106)(H,113,114)(H4,79,80,85)(H4,81,82,86)(H4,83,84,87)
• InChIKey: OVVIBUHLQIYUEU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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]hexanoic acid
• IUPAC Traditional name: 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]hexanoic acid
• Synonyms: Dynorphin A Porcine Fragment 1-13; [D-Arg6]-Dynorphin A Porcine fragment 1-13

Database IDs

• CAS Number: 72957-38-1; 75921-87-8
• MDL Number: MFCD00076369; MFCD00076366
• PubChem SID: 24894260; 162227172; 24894071
• PubChem CID: 25081031

CALCULATED PROPERTIES

• Acid pKa: 3.6786067
• H Acceptors: 27
• H Donor: 25
• LogD (pH = 5.5): -18.729204
• LogD (pH = 7.4): -16.202692
• Log P: -8.108618
• Molar Refractivity: 453.8319 cm^3
• Polarizability: 164.69804 Å^3
• Polar Surface Area: 661.7 Å^2
• Rotatable Bonds: 54
• 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

Pharmacology Properties

• Gene Information: pig ... PDYN(445529)

Product Information

• Purity: ≥97% (HPLC)
• Compostion: Peptide content, ~60%; Peptide content, ~70%
• Empirical Formula (Hill Notation): C75H126N24O15

DETAILS

Sigma Aldrich - D9148

Amino Acid Sequence
Tyr-Gly-Gly-Phe-Leu-D-Arg-Arg-Ile-Arg-Pro-Lys-Leu-Lys
Biochem/physiol Actions
κ opioid receptor agonist; anticonvulsant

Sigma Aldrich - D7017

Amino Acid Sequence
Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Ile-Arg-Pro-Lys-Leu-Lys
Biochem/physiol Actions
Potent, endogenous κ-agonist.