(4S)-4-(hydroxymethyl)-1,3-oxazolidine-2,5-dione

• ChemBase ID: 177737
• Molecular Formular: C4H5NO4
• Molecular Mass: 131.0868
• Monoisotopic Mass: 131.02185765
• SMILES: O1C(=O)[C@@H](NC1=O)CO
• Canonical SMILES: OC[C@@H]1NC(=O)OC1=O
• InChI: InChI=1S/C4H5NO4/c6-1-2-3(7)9-4(8)5-2/h2,6H,1H2,(H,5,8)/t2-/m0/s1
• InChIKey: KVUIJQRUDVLWAI-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-(hydroxymethyl)-1,3-oxazolidine-2,5-dione
• IUPAC Traditional name: (4S)-4-(hydroxymethyl)-1,3-oxazolidine-2,5-dione
• Synonyms: (4S)-4-(Hydroxymethyl)-2,5-oxazolidinedione; (S)-4-(Hydroxymethyl)-2,5-oxazolidinedione; L-4-(Hydroxymethyl)-2,5-oxazolidinedione; Ser-NCA; L-Serine N-Carboxyanhydride

Database IDs

• CAS Number: 33043-54-8
• PubChem SID: 164233647
• PubChem CID: 55286273

CALCULATED PROPERTIES

• Acid pKa: 11.031383
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.96587336
• LogD (pH = 7.4): -0.9659622
• Log P: -1.1992056
• Molar Refractivity: 25.1339 cm^3
• Polarizability: 10.258732 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S271020

An amino acid N-carboxyanhydride useful in the prearation of polypeptides as antiinflammatory agents.

REFERENCES

• Kramer, et al.: J. Biochem., 269, 10621 (1994)
• Oh, D., et al.: Pharma. Biotechnol., 1999, 12, 59 (1994)
• Knutter, I., et al.: Biochemistry, 40, 4454 (1994)