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

• ChemBase ID: 128642
• Molecular Formular: C23H24N4O9
• Molecular Mass: 500.45806
• Monoisotopic Mass: 500.15432837
• SMILES: O=C(O)[C@@H](c1ccc(O)cc1)N1C(=O)[C@@H](NC(=O)/C(=N/O)/c2ccc(OCC[C@H](C(=O)O)N)cc2)C1
• Canonical SMILES: O/N=C(\c1ccc(cc1)OCC[C@H](C(=O)O)N)/C(=O)N[C@H]1CN(C1=O)[C@H](c1ccc(cc1)O)C(=O)O
• InChI: InChI=1S/C23H24N4O9/c24-16(22(31)32)9-10-36-15-7-3-12(4-8-15)18(26-35)20(29)25-17-11-27(21(17)30)19(23(33)34)13-1-5-14(28)6-2-13/h1-8,16-17,19,28,35H,9-11,24H2,(H,25,29)(H,31,32)(H,33,34)/t16-,17+,19-/m1/s1
• InChIKey: CTNZOGJNVIFEBA-ZIFCJYIRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-4-[4-({[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl}(hydroxyimino)methyl)phenoxy]butanoic acid
• IUPAC Traditional name: (2R)-2-amino-4-[4-({[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl}(hydroxyimino)methyl)phenoxy]butanoic acid
• Synonyms: Nocardicin A

Database IDs

• CAS Number: 39391-39-4
• PubChem SID: 162222949
• PubChem CID: 6419429
• Chemspider ID: 4925179
• Wikipedia Title: Nocardicin_A

CALCULATED PROPERTIES

• Acid pKa: 1.7427144
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -4.735509
• LogD (pH = 7.4): -6.9160576
• Log P: -2.4572067
• Molar Refractivity: 121.8045 cm^3
• Polarizability: 47.32011 Å^3
• Polar Surface Area: 212.08 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false