1-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]-4-(methylsulfanyl)butanamido}acetamido)-3-phenylpropanoyl]pyrrolidine-2-carboxamide

• ChemBase ID: 103786
• Molecular Formular: C30H40N6O6S
• Molecular Mass: 612.7402
• Monoisotopic Mass: 612.27300403
• SMILES: CSCCC(NC(=O)C(N)Cc1ccc(O)cc1)C(=O)NCC(=O)NC(Cc1ccccc1)C(=O)N1CCCC1C(=O)N
• Canonical SMILES: CSCCC(C(=O)NCC(=O)NC(C(=O)N1CCCC1C(=O)N)Cc1ccccc1)NC(=O)C(Cc1ccc(cc1)O)N
• InChI: InChI=1S/C30H40N6O6S/c1-43-15-13-23(35-28(40)22(31)16-20-9-11-21(37)12-10-20)29(41)33-18-26(38)34-24(17-19-6-3-2-4-7-19)30(42)36-14-5-8-25(36)27(32)39/h2-4,6-7,9-12,22-25,37H,5,8,13-18,31H2,1H3,(H2,32,39)(H,33,41)(H,34,38)(H,35,40)
• InChIKey: UIRWGVLTPPSGEN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]-4-(methylsulfanyl)butanamido}acetamido)-3-phenylpropanoyl]pyrrolidine-2-carboxamide
• IUPAC Traditional name: 1-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]-4-(methylsulfanyl)butanamido}acetamido)-3-phenylpropanoyl]pyrrolidine-2-carboxamide
• Synonyms: Tyr-D-Met-Gly-Phe-Pro-NH₂; [D-Met^2, Pro^5]-ENKEPHALINAMIDE

Database IDs

• CAS Number: 63307-63-1
• PubChem SID: 162091352
• PubChem CID: 13174931

CALCULATED PROPERTIES

• Acid pKa: 9.509703
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -2.3395708
• LogD (pH = 7.4): -0.6687679
• Log P: -0.30755717
• Molar Refractivity: 163.0119 cm^3
• Polarizability: 63.629078 Å^3
• Polar Surface Area: 196.95 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 02152834

A highly active analog of [Met5]-enkephalin which is more resistant to proteolytic degradation.
This product has a molar potency ratio of 5.5 relative to morphine.

REFERENCES

• Bejusz, S., et al., FEBS Lett., 76: 91 (1977).