2-{2-[2-(2-aminoacetamido)acetamido]-3-phenylpropanamido}-4-(methylsulfanyl)butanoic acid

• ChemBase ID: 105501
• Molecular Formular: C18H26N4O5S
• Molecular Mass: 410.48784
• Monoisotopic Mass: 410.16239095
• SMILES: CSCCC(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CN)C(=O)O
• Canonical SMILES: NCC(=O)NCC(=O)NC(C(=O)NC(C(=O)O)CCSC)Cc1ccccc1
• InChI: InChI=1S/C18H26N4O5S/c1-28-8-7-13(18(26)27)22-17(25)14(9-12-5-3-2-4-6-12)21-16(24)11-20-15(23)10-19/h2-6,13-14H,7-11,19H2,1H3,(H,20,23)(H,21,24)(H,22,25)(H,26,27)
• InChIKey: KWHAJHJQOWBJEG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[2-(2-aminoacetamido)acetamido]-3-phenylpropanamido}-4-(methylsulfanyl)butanoic acid
• IUPAC Traditional name: 2-{2-[2-(2-aminoacetamido)acetamido]-3-phenylpropanamido}-4-(methylsulfanyl)butanoic acid
• Synonyms: [Des-Tyr^1,Met^5]-ENKEPHALIN

Database IDs

• CAS Number: 61370-88-5
• PubChem SID: 162093622
• PubChem CID: 14598600

CALCULATED PROPERTIES

• Acid pKa: 3.6128852
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.2824595
• LogD (pH = 7.4): -3.402424
• Log P: -3.2833185
• Molar Refractivity: 105.1094 cm^3
• Polarizability: 41.23339 Å^3
• Polar Surface Area: 150.62 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 02190433

(β-Lipotropin 62-65; Gly-Gly-Phe-Met)
An enkephalinase inhibitor.

REFERENCES

• Malfroy, B., et al., Nature, 276: 523 (1978).
• Fournie-Zaluski, M.C., et al., Biochem. Biophys. Res. Commun., 91: 130 (1979).
• • Swerts, J