(2S)-2-{[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-7-acetamido-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid

• ChemBase ID: 161380
• Molecular Formular: C25H29NO8
• Molecular Mass: 471.49966
• Monoisotopic Mass: 471.18931689
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]2[C@H]1OC(OC2)c1ccccc1)OCc1ccccc1)NC(=O)C)O[C@@H](C)C(=O)O
• Canonical SMILES: CC(=O)N[C@@H]1[C@@H](OCc2ccccc2)O[C@H]2[C@H]([C@@H]1O[C@H](C(=O)O)C)OC(OC2)c1ccccc1
• InChI: InChI=1S/C25H29NO8/c1-15(23(28)29)32-22-20(26-16(2)27)25(30-13-17-9-5-3-6-10-17)33-19-14-31-24(34-21(19)22)18-11-7-4-8-12-18/h3-12,15,19-22,24-25H,13-14H2,1-2H3,(H,26,27)(H,28,29)/t15-,19+,20+,21+,22+,24?,25-/m0/s1
• InChIKey: JPPMVSNCFXDOJX-WAUMRMSNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-7-acetamido-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid
• IUPAC Traditional name: (2S)-2-{[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-7-acetamido-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid
• Synonyms: N-Acetyl-1-O-(phenylmethyl)-4,6-O-(phenylmethylene)-α-isomuramic Acid; Benzyl N-Acetyl-4,6-O-benzylidene-α-isomuramic Acid

Database IDs

• CAS Number: 730911-70-3
• PubChem SID: 162255515
• PubChem CID: 2735221

CALCULATED PROPERTIES

• Acid pKa: 3.5032012
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 1.0133623
• LogD (pH = 7.4): -0.37245753
• Log P: 3.0019784
• Molar Refractivity: 118.6018 cm^3
• Polarizability: 47.653275 Å^3
• Polar Surface Area: 112.55 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B223240

A derivative of isomuramic acid.

REFERENCES

• Gross, P.: Liebigs Ann. Chem. 1, 37 (1986)