(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-methylpentanoic acid

• ChemBase ID: 134387
• Molecular Formular: C46H72N14O10
• Molecular Mass: 981.15168
• Monoisotopic Mass: 980.55558457
• SMILES: CC[C@H](C)[C@@H](C(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N)CC(C)C)CCCNC(=N)N)CCCNC(=N)N)C
• InChI: InChI=1S/C46H72N14O10/c1-5-27(4)38(44(69)70)60-41(66)33(14-10-20-53-46(50)51)57-40(65)32(13-9-19-52-45(48)49)58-42(67)34(21-26(2)3)59-43(68)35(23-28-11-7-6-8-12-28)56-37(63)25-54-36(62)24-55-39(64)31(47)22-29-15-17-30(61)18-16-29/h6-8,11-12,15-18,26-27,31-35,38,61H,5,9-10,13-14,19-25,47H2,1-4H3,(H,54,62)(H,55,64)(H,56,63)(H,57,65)(H,58,67)(H,59,68)(H,60,66)(H,69,70)(H4,48,49,52)(H4,50,51,53)/t27-,31-,32-,33-,34-,35-,38-/m0/s1
• InChIKey: WRPLGMBDXVBPEG-VGXZEHLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-methylpentanoic acid
• IUPAC Traditional name: (2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-methylpentanoic acid
• Synonyms: Dynorphin A Porcine Fragment 1-8

Database IDs

• CAS Number: 75790-53-3
• MDL Number: MFCD00076357
• PubChem SID: 24893905; 162228663
• PubChem CID: 10486131

CALCULATED PROPERTIES

• Log P: -5.4681644
• Molar Refractivity: 277.932 cm^3
• Polarizability: 99.827965 Å^3
• Polar Surface Area: 411.05 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false
• Acid pKa: 3.559637
• H Acceptors: 17
• H Donor: 16
• LogD (pH = 5.5): -7.9346747
• LogD (pH = 7.4): -6.252719

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: human ... OPRD1(4985), OPRK1(4986), OPRM1(4988)pig ... PDYN(445529)rat ... Oprd1(24613), Oprm1(25601)

Product Information

• Purity: ≥97% (HPLC)
• Compostion: Peptide content, ~70%

DETAILS

Sigma Aldrich - D4899

Amino Acid Sequence
Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Ile
Biochem/physiol Actions
Potent κ opioid agonist; its agonist activity at μ and δ receptors may be due to hydrolysis of the peptide by proteases in the membrane or cell preparations.