2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanoic acid

• ChemBase ID: 105500
• Molecular Formular: C27H35N5O7S
• Molecular Mass: 573.6611
• Monoisotopic Mass: 573.22571949
• SMILES: CSCCC(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(N)Cc1ccc(O)cc1)C(=O)O
• Canonical SMILES: CSCCC(C(=O)O)NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(Cc1ccc(cc1)O)N
• InChI: InChI=1S/C27H35N5O7S/c1-40-12-11-21(27(38)39)32-26(37)22(14-17-5-3-2-4-6-17)31-24(35)16-29-23(34)15-30-25(36)20(28)13-18-7-9-19(33)10-8-18/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39)
• InChIKey: YFGBQHOOROIVKG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanoic acid
• IUPAC Traditional name: met-enkephalin
• Synonyms: [Methionine]enkephalin; L-Tyrosylglycylglycyl-L-phenylalanyl-L-methionine; Met-enkephalin; Methionine Enkephalin; Tyr-Gly-Gly-Phe-Met; (Met5)-ENKEPHALIN

Database IDs

• CAS Number: 58569-55-4
• EC Number: 261-335-8
• PubChem SID: 162092632
• PubChem CID: 6427062; 42785
• CHEMBL: 13786
• Chemspider ID: 391597
• KEGG ID: C11684
• MeSH Name: Enkephalin,+Methionine
• Wikipedia Title: Met-enkephalin

CALCULATED PROPERTIES

• Acid pKa: 3.6128778
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -2.4654956
• LogD (pH = 7.4): -2.6164544
• Log P: -2.4675272
• Molar Refractivity: 149.0067 cm^3
• Polarizability: 58.17051 Å^3
• Polar Surface Area: 199.95 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Partition Coefficient: 0.607
• pKa: 3.234
• pKb: 10.763

Safety Information

• Storage Condition: -20°C
• RTECS: AV8300000

DETAILS

MP Biomedicals - 02190430

Endogenous opioid pentapeptide.

REFERENCES

• Hughes, J., et al., 258 , 577 (1975).