methyl (4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

• ChemBase ID: 92242
• Molecular Formular: C12H21NO9
• Molecular Mass: 323.29644
• Monoisotopic Mass: 323.12163126
• SMILES: COC(=O)C1(O)C[C@H](O)[C@@H](NC(=O)C)[C@@H](O1)[C@H](O)[C@H](O)CO
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1OC(O)(C[C@@H]([C@H]1NC(=O)C)O)C(=O)OC)O)O
• InChI: InChI=1S/C12H21NO9/c1-5(15)13-8-6(16)3-12(20,11(19)21-2)22-10(8)9(18)7(17)4-14/h6-10,14,16-18,20H,3-4H2,1-2H3,(H,13,15)/t6-,7+,8+,9+,10+,12?/m0/s1
• InChIKey: BKZQMWNJESHHSA-PQYSTZNASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• Synonyms: N-Acetylneuraminic acid , methyl ester

Database IDs

• CAS Number: 50998-13-5
• MDL Number: MFCD00214229
• PubChem SID: 162078940
• PubChem CID: 10734675

CALCULATED PROPERTIES

• Acid pKa: 9.561499
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.4180818
• LogD (pH = 7.4): -3.4210243
• Log P: -3.4180434
• Molar Refractivity: 68.5505 cm^3
• Polarizability: 28.28038 Å^3
• Polar Surface Area: 165.78 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 193.5-194.5°C