2-{2-[2-(2-amino-3-methylbutanamido)acetamido]-3-carboxypropanamido}pentanedioic acid

• ChemBase ID: 103762
• Molecular Formular: C16H26N4O9
• Molecular Mass: 418.39904
• Monoisotopic Mass: 418.16997843
• SMILES: CC(C)C(N)C(=O)NCC(=O)NC(CC(=O)O)C(=O)NC(CCC(=O)O)C(=O)O
• Canonical SMILES: O=C(NC(C(=O)NC(C(=O)O)CCC(=O)O)CC(=O)O)CNC(=O)C(C(C)C)N
• InChI: InChI=1S/C16H26N4O9/c1-7(2)13(17)15(27)18-6-10(21)19-9(5-12(24)25)14(26)20-8(16(28)29)3-4-11(22)23/h7-9,13H,3-6,17H2,1-2H3,(H,18,27)(H,19,21)(H,20,26)(H,22,23)(H,24,25)(H,28,29)
• InChIKey: UNOPRHLQSPTPBF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[2-(2-amino-3-methylbutanamido)acetamido]-3-carboxypropanamido}pentanedioic acid
• IUPAC Traditional name: 2-{2-[2-(2-amino-3-methylbutanamido)acetamido]-3-carboxypropanamido}pentanedioic acid
• Synonyms: Eosinophilotactic Tetrapeptide; VGAG; VAL-GLY-ASP-GLU

Database IDs

• CAS Number: 63141-66-2
• PubChem SID: 162091397
• PubChem CID: 14496748

CALCULATED PROPERTIES

• Acid pKa: 2.8000515
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -8.786546
• LogD (pH = 7.4): -11.82625
• Log P: -5.404108
• Molar Refractivity: 93.716995 cm^3
• Polarizability: 37.32312 Å^3
• Polar Surface Area: 225.22 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 0°C

REFERENCES

• Goetzl, E.J. and Austen, F., Proc. Natl. Acad. Sci. USA, 72: 4123, (1975).
• Turnbull, L.W., et al., Immunology, 32: 57, (1977).
• Beswick, P.H. and Kay, A.B., Clin. Exp Immunol., 43: 399, (1981).