(2R)-2-amino-4-[4-({[(3S)-1-[(S)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl}carbonyl)phenoxy]butanoic acid

• ChemBase ID: 175542
• Molecular Formular: C23H23N3O9
• Molecular Mass: 485.44342
• Monoisotopic Mass: 485.14342933
• SMILES: c1(ccc(cc1)C(=O)C(=O)N[C@H]1CN(C1=O)[C@@H](c1ccc(cc1)O)C(=O)O)OCC[C@@H](N)C(=O)O
• Canonical SMILES: Oc1ccc(cc1)[C@H](N1C[C@@H](C1=O)NC(=O)C(=O)c1ccc(cc1)OCC[C@H](C(=O)O)N)C(=O)O
• InChI: InChI=1S/C23H23N3O9/c24-16(22(31)32)9-10-35-15-7-3-13(4-8-15)19(28)20(29)25-17-11-26(21(17)30)18(23(33)34)12-1-5-14(27)6-2-12/h1-8,16-18,27H,9-11,24H2,(H,25,29)(H,31,32)(H,33,34)/t16-,17+,18+/m1/s1
• InChIKey: QJZHIGKJGFPGRN-SQNIBIBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-4-[4-({[(3S)-1-[(S)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl}carbonyl)phenoxy]butanoic acid
• IUPAC Traditional name: (2R)-2-amino-4-[4-({[(3S)-1-[(S)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl}carbonyl)phenoxy]butanoic acid
• Synonyms: (αR,3S)-3-[[[4-[(3R)-3-Amino-3-carboxypropoxy]phenyl]oxoacetyl]amino]-α-(4-hydroxyphenyl)-2-oxo-1-azetidineacetic Acid; Nocardicin D

Database IDs

• CAS Number: 61425-17-0
• PubChem SID: 164231452
• PubChem CID: 71751152

CALCULATED PROPERTIES

• Acid pKa: 1.6578132
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.682341
• LogD (pH = 7.4): -5.7673697
• Log P: -2.44501
• Molar Refractivity: 117.9828 cm^3
• Polarizability: 45.954063 Å^3
• Polar Surface Area: 196.56 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N634020

Nocardicin D is a β-lactam antibiotic.

REFERENCES

• Hosoda, J., et al.: Agric. Biol. Chem., 41, 2013 (1977)