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

• ChemBase ID: 3011
• Molecular Formular: C11H18N2O7
• Molecular Mass: 290.26982
• Monoisotopic Mass: 290.11140093
• SMILES: CC(=O)N[C@@H]1[C@@H](N)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)N)C(=O)O)O)O
• InChI: InChI=1S/C11H18N2O7/c1-4(15)13-8-5(12)2-7(11(18)19)20-10(8)9(17)6(16)3-14/h2,5-6,8-10,14,16-17H,3,12H2,1H3,(H,13,15)(H,18,19)/t5-,6-,8+,9+,10+/m0/s1
• InChIKey: NKENBBIXEGPQLS-CUZACWQJSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 160966458; 46508941
• PubChem CID: 46936641

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3003387
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -6.059817
• LogD (pH = 7.4): -6.09289
• Log P: -6.0592656
• Molar Refractivity: 65.7682 cm^3
• Polarizability: 26.099392 Å^3
• Polar Surface Area: 162.34 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.95
• LOG S: -0.7
• Solubility (Water): 5.80e+01 g/l

DETAILS

DrugBank - DB03321

Drug information: experimental