2-{2-[2-formamido-4-(methylsulfanyl)butanamido]-4-methylpentanamido}-3-phenylpropanoic acid

• ChemBase ID: 103278
• Molecular Formular: C21H31N3O5S
• Molecular Mass: 437.55294
• Monoisotopic Mass: 437.19844211
• SMILES: CSCCC(NC=O)C(=O)NC(CC(C)C)C(=O)NC(Cc1ccccc1)C(=O)O
• Canonical SMILES: CSCCC(C(=O)NC(C(=O)NC(C(=O)O)Cc1ccccc1)CC(C)C)NC=O
• InChI: InChI=1S/C21H31N3O5S/c1-14(2)11-17(23-19(26)16(22-13-25)9-10-30-3)20(27)24-18(21(28)29)12-15-7-5-4-6-8-15/h4-8,13-14,16-18H,9-12H2,1-3H3,(H,22,25)(H,23,26)(H,24,27)(H,28,29)
• InChIKey: PRQROPMIIGLWRP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[2-formamido-4-(methylsulfanyl)butanamido]-4-methylpentanamido}-3-phenylpropanoic acid
• IUPAC Traditional name: 2-{2-[2-formamido-4-(methylsulfanyl)butanamido]-4-methylpentanamido}-3-phenylpropanoic acid
• Synonyms: Chemotactic peptide; N-Formyl-L-methionyl-L-leucyl-L-phenylalanine; N-FORMYL-MET-LEU-PHE

Database IDs

• CAS Number: 59880-97-6
• PubChem SID: 162090572
• PubChem CID: 4364

CALCULATED PROPERTIES

• Acid pKa: 3.99377
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.16479339
• LogD (pH = 7.4): -1.4823759
• Log P: 1.6802635
• Molar Refractivity: 115.4267 cm^3
• Polarizability: 45.200108 Å^3
• Polar Surface Area: 124.6 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 213-216°C

Safety Information

• Storage Condition: -20°C

REFERENCES

• Aswanikumar, S., et al., J. Exp. Med., 143: 1154 (1976).
• Aswanikumar, S., et al., Biochem. Biophys. Res. Commun., 74: 810 (1977).
• O'Dea, R.F., Nature, 272: 462 (1978).
• Niedel, J., et al., J.