(2S)-2-[(3S)-3-[(2Z)-2-(N-hydroxyimino)-2-(4-hydroxyphenyl)acetamido]-2-oxoazetidin-1-yl]-2-(4-hydroxyphenyl)acetic acid

• ChemBase ID: 175543
• Molecular Formular: C19H17N3O7
• Molecular Mass: 399.35418
• Monoisotopic Mass: 399.1066499
• SMILES: c1(ccc(cc1)/C(=N/O)/C(=O)N[C@H]1CN(C1=O)[C@@H](c1ccc(cc1)O)C(=O)O)O
• Canonical SMILES: O/N=C(\C(=O)N[C@H]1CN(C1=O)[C@@H](c1ccc(cc1)O)C(=O)O)/c1ccc(cc1)O
• InChI: InChI=1S/C19H17N3O7/c23-12-5-1-10(2-6-12)15(21-29)17(25)20-14-9-22(18(14)26)16(19(27)28)11-3-7-13(24)8-4-11/h1-8,14,16,23-24,29H,9H2,(H,20,25)(H,27,28)/b21-15-/t14-,16-/m0/s1
• InChIKey: NMMOYDKOFASOBV-AHQJNRKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(3S)-3-[(2Z)-2-(N-hydroxyimino)-2-(4-hydroxyphenyl)acetamido]-2-oxoazetidin-1-yl]-2-(4-hydroxyphenyl)acetic acid
• IUPAC Traditional name: (S)-[(3S)-3-[(2Z)-2-(N-hydroxyimino)-2-(4-hydroxyphenyl)acetamido]-2-oxoazetidin-1-yl](4-hydroxyphenyl)acetic acid
• Synonyms: (αR,3S)-3-[[(2Z)-(Hydroxyimino)(4-hydroxyphenyl)acetyl]amino]-α-(4-hydroxyphenyl)-2-oxo-1-azetidineacetic Acid; [3S-[1(S*),3R*(Z)]]-3-[[(Hydroxyimino)(4-hydroxyphenyl)acetyl]amino]-α-(4-hydroxyphenyl)-2-oxo-1-azetidineacetic Acid; Nocardicin E

Database IDs

• CAS Number: 63555-59-9
• PubChem SID: 164231453
• PubChem CID: 71751153

CALCULATED PROPERTIES

• Acid pKa: 3.0681317
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.5952381
• LogD (pH = 7.4): -3.7843094
• Log P: 0.88280696
• Molar Refractivity: 98.6771 cm^3
• Polarizability: 37.781822 Å^3
• Polar Surface Area: 159.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N634040

Nocardicin E is a β-lactam antibiotic.

REFERENCES

• Aoki, H., et al.: J. Antibiot., 29, 492 (1976)
• Mendez, R., et al.: Chem. Pharm. Bull., 40, 3222 (1976)
• Reeve, A., et al.: J. Biol. Chem., 273, 30695 (1976)