3-{[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}propanoic acid

• ChemBase ID: 177951
• Molecular Formular: C13H15NO6
• Molecular Mass: 281.2613
• Monoisotopic Mass: 281.08993721
• SMILES: c1c(ccc(c1)C[C@H](NC(=O)CCC(=O)O)C(=O)O)O
• Canonical SMILES: O=C(N[C@H](C(=O)O)Cc1ccc(cc1)O)CCC(=O)O
• InChI: InChI=1S/C13H15NO6/c15-9-3-1-8(2-4-9)7-10(13(19)20)14-11(16)5-6-12(17)18/h1-4,10,15H,5-7H2,(H,14,16)(H,17,18)(H,19,20)/t10-/m0/s1
• InChIKey: ZMLAEOWQOQIWJT-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: 3-{[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}propanoic acid
• Synonyms: N-(3-Carboxy-1-oxopropyl)-L-tyrosine; Clavulanic Acid Impurity G; N-Succinyl-L-tyrosine

Database IDs

• CAS Number: 374816-32-7
• PubChem SID: 164233861
• PubChem CID: 9900373

CALCULATED PROPERTIES

• Acid pKa: 3.3782084
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -3.0135145
• LogD (pH = 7.4): -6.0661817
• Log P: 0.4177591
• Molar Refractivity: 67.4343 cm^3
• Polarizability: 26.217249 Å^3
• Polar Surface Area: 123.93 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S692150

A by-product formed during the fermentation leading to Clavulanic acid.

REFERENCES

• Babbitt, P., et al.: Science, 267, 1159 (1995)
• Perona, J., et al.: J. Biol. Chem., 272, 29987 (1995)
• Palmer, D., et al.: Biochemistry, 38, 4252 (1995)