(2S)-2-[(3S)-3-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-2-oxoazetidin-1-yl]-2-(4-hydroxyphenyl)acetic acid

• ChemBase ID: 175545
• Molecular Formular: C19H19N3O6
• Molecular Mass: 385.37066
• Monoisotopic Mass: 385.12738534
• SMILES: c1(ccc(cc1)[C@@H](N)C(=O)N[C@H]1CN(C1=O)[C@@H](c1ccc(cc1)O)C(=O)O)O
• Canonical SMILES: Oc1ccc(cc1)[C@H](C(=O)N[C@H]1CN(C1=O)[C@@H](c1ccc(cc1)O)C(=O)O)N
• InChI: InChI=1S/C19H19N3O6/c20-15(10-1-5-12(23)6-2-10)17(25)21-14-9-22(18(14)26)16(19(27)28)11-3-7-13(24)8-4-11/h1-8,14-16,23-24H,9,20H2,(H,21,25)(H,27,28)/t14-,15+,16-/m0/s1
• InChIKey: SAVAPYNOQXYBJS-XHSDSOJGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(3S)-3-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-2-oxoazetidin-1-yl]-2-(4-hydroxyphenyl)acetic acid
• IUPAC Traditional name: (S)-[(3S)-3-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-2-oxoazetidin-1-yl](4-hydroxyphenyl)acetic acid
• Synonyms: (αR,3S)-3-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-α-(4-hydroxyphenyl)-2-oxo-1-azetidineacetic Acid; [3S-[1(S*),3R*(S*)]]-3-[[Amino(4-hydroxyphenyl)acetyl]amino]-α-(4-hydroxyphenyl)-2-oxo-1-azetidineacetic Acid; Antibiotic FR 29644; FR 29644; Nocardicin G

Database IDs

• CAS Number: 65309-11-7
• PubChem SID: 164231455
• PubChem CID: 13942923

CALCULATED PROPERTIES

• Acid pKa: 3.0554538
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.0936182
• LogD (pH = 7.4): -2.3581088
• Log P: -2.0930903
• Molar Refractivity: 96.961 cm^3
• Polarizability: 37.832565 Å^3
• Polar Surface Area: 153.19 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N634080

Nocardicin G 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)