2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido}-3-hydroxybutanoic acid

• ChemBase ID: 103780
• Molecular Formular: C33H46N6O10
• Molecular Mass: 686.75254
• Monoisotopic Mass: 686.3275417
• SMILES: CC(C)CC(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)C(CO)NC(=O)C(N)Cc1ccc(O)cc1)C(=O)NC(C(C)O)C(=O)O
• Canonical SMILES: OCC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)C(O)C)CC(C)C)Cc1ccccc1)NC(=O)C(Cc1ccc(cc1)O)N
• InChI: InChI=1S/C33H46N6O10/c1-18(2)13-24(32(47)39-28(19(3)41)33(48)49)37-31(46)25(15-20-7-5-4-6-8-20)36-27(43)16-35-30(45)26(17-40)38-29(44)23(34)14-21-9-11-22(42)12-10-21/h4-12,18-19,23-26,28,40-42H,13-17,34H2,1-3H3,(H,35,45)(H,36,43)(H,37,46)(H,38,44)(H,39,47)(H,48,49)
• InChIKey: PKSODCLCMBUCPW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido}-3-hydroxybutanoic acid
• IUPAC Traditional name: 2-{2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido}-3-hydroxybutanoic acid
• Synonyms: Δ-Opiate Receptor Peptide; DSLET; Tyr-D-Ser-Gly-Phe-Leu-Thr; [D-Ser^2, Leu^5]-ENKEPHALIN-Thr

Database IDs

• CAS Number: 75644-90-5
• PubChem SID: 162103108
• PubChem CID: 4291056

CALCULATED PROPERTIES

• Acid pKa: 3.564238
• H Acceptors: 11
• H Donor: 10
• LogD (pH = 5.5): -3.5079496
• LogD (pH = 7.4): -3.6594932
• Log P: -3.5103192
• Molar Refractivity: 174.8891 cm^3
• Polarizability: 68.68641 Å^3
• Polar Surface Area: 269.51 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

DETAILS

MP Biomedicals - 02152816

Exhibits a very high specificity for δ-opiate receptors.

REFERENCES

• Gacel, G., et al., FEBS Lett., 118: 245 (1980).
• Fournie-Zaluski, M.C., et al., Mol. Pharmac. , 20: 484 (1980).
• Gacel, G., et al., J. Med. Chem., 24: 1119 (1981).
• Chesselet, M.F., et al., Nature, 291: 320 (1981).
• David, M., et al., Eur. J. Pharmac. , 78: 385 (1982).