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

• ChemBase ID: 103763
• Molecular Formular: C15H26N4O8
• Molecular Mass: 390.38894
• Monoisotopic Mass: 390.17506381
• SMILES: CC(C)C(N)C(=O)NCC(=O)NC(CO)C(=O)NC(CCC(=O)O)C(=O)O
• Canonical SMILES: OCC(C(=O)NC(C(=O)O)CCC(=O)O)NC(=O)CNC(=O)C(C(C)C)N
• InChI: InChI=1S/C15H26N4O8/c1-7(2)12(16)14(25)17-5-10(21)18-9(6-20)13(24)19-8(15(26)27)3-4-11(22)23/h7-9,12,20H,3-6,16H2,1-2H3,(H,17,25)(H,18,21)(H,19,24)(H,22,23)(H,26,27)
• InChIKey: KDZIGQIDPXKMBA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 61756-22-7
• PubChem SID: 162103277
• PubChem CID: 336414

CALCULATED PROPERTIES

• Acid pKa: 3.0305855
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -7.257922
• LogD (pH = 7.4): -8.863783
• Log P: -5.8094726
• Molar Refractivity: 89.225296 cm^3
• Polarizability: 35.506443 Å^3
• Polar Surface Area: 208.15 Å^2
• Rotatable Bonds: 12
• 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).