(2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2S)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid

• ChemBase ID: 3621
• Molecular Formular: C11H17NO8
• Molecular Mass: 291.25458
• Monoisotopic Mass: 291.09541651
• SMILES: CC(=O)N[C@@H]1[C@@H](O)C=C(O[C@H]1[C@H](O)[C@@H](O)CO)C(=O)O
• Canonical SMILES: OC[C@@H]([C@H]([C@@H]1OC(=C[C@@H]([C@H]1NC(=O)C)O)C(=O)O)O)O
• InChI: InChI=1S/C11H17NO8/c1-4(14)12-8-5(15)2-7(11(18)19)20-10(8)9(17)6(16)3-13/h2,5-6,8-10,13,15-17H,3H2,1H3,(H,12,14)(H,18,19)/t5-,6-,8+,9+,10+/m0/s1
• InChIKey: JINJZWSZQKHCIP-CUZACWQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2S)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• IUPAC Traditional name: (4S,5R,6R)-5-acetamido-4-hydroxy-6-[(1R,2S)-1,2,3-trihydroxypropyl]-5,6-dihydro-4H-pyran-2-carboxylic acid
• Synonyms: 2-Deoxy-2,3-Dehydro-N-Acetyl-Neuraminic Acid

Database IDs

• PubChem SID: 160967059; 46505061
• PubChem CID: 13728878

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.517408
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -5.7103395
• LogD (pH = 7.4): -7.0726504
• Log P: -3.688152
• Molar Refractivity: 64.1107 cm^3
• Polarizability: 25.284155 Å^3
• Polar Surface Area: 156.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.2
• LOG S: -0.65
• Solubility (Water): 6.52e+01 g/l

DETAILS

DrugBank - DB03991

Drug information: experimental