(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

• ChemBase ID: 175199
• Molecular Formular: C29H27N2O10P
• Molecular Mass: 594.505841
• Monoisotopic Mass: 594.1403317
• SMILES: [C@H]12[C@H](C(=C(N1C(=O)[C@@H]2[C@H](O)C)C(=O)OCc1ccc(cc1)[N+](=O)[O-])OP(=O)(Oc1ccccc1)Oc1ccccc1)C
• Canonical SMILES: C[C@H]([C@H]1C(=O)N2[C@@H]1[C@@H](C)C(=C2C(=O)OCc1ccc(cc1)[N+](=O)[O-])OP(=O)(Oc1ccccc1)Oc1ccccc1)O
• InChI: InChI=1S/C29H27N2O10P/c1-18-25-24(19(2)32)28(33)30(25)26(29(34)38-17-20-13-15-21(16-14-20)31(35)36)27(18)41-42(37,39-22-9-5-3-6-10-22)40-23-11-7-4-8-12-23/h3-16,18-19,24-25,32H,17H2,1-2H3/t18-,19-,24-,25-/m1/s1
• InChIKey: STULDTCHQXVRIX-PIYXRGFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• IUPAC Traditional name: (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• Synonyms: (4R,5R,6S)-3-[(Diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid (4-Nitrophenyl)methyl Ester; 4-Nitrobenzyl (4R,5S,6S)-3-[(Diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; beta-Methyl vinyl phosphate

Database IDs

• CAS Number: 90776-59-3
• PubChem SID: 164231109
• PubChem CID: 10304013

CALCULATED PROPERTIES

• Acid pKa: 14.997331
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 4.0510654
• LogD (pH = 7.4): 4.0510654
• Log P: 4.0510654
• Molar Refractivity: 149.2912 cm^3
• Polarizability: 57.97547 Å^3
• Polar Surface Area: 154.74 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 129-131°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

Product Information

• Purity: 95+%

REFERENCES

• Sunagawa, M., et al.: J. Antibiot., 43, 519 (1990)
• Wiseman, L., et al.: Drugs, 50, 73 (1990)
• Blumer, J., et al.: Int. J. Antimicrob. Agents, 8, 73 (1990)