(2R,4S,5R,6R)-2-(benzyloxy)-5-(2H3)acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 159165
• Molecular Formular: C18H25NO9
• Molecular Mass: 399.3924
• Monoisotopic Mass: 399.15293139
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@](O1)(OCc1ccccc1)C(=O)O)O)NC(=O)C)[C@@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@](OCc2ccccc2)(C[C@H]([C@H]1NC(=O)C)O)C(=O)O)O)O
• InChI: InChI=1S/C18H25NO9/c1-10(21)19-14-12(22)7-18(17(25)26,27-9-11-5-3-2-4-6-11)28-16(14)15(24)13(23)8-20/h2-6,12-16,20,22-24H,7-9H2,1H3,(H,19,21)(H,25,26)/t12-,13+,14+,15+,16+,18+/m0/s1
• InChIKey: USDSFROVJNDKEX-DGYIVEFISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R,6R)-2-(benzyloxy)-5-(^2H₃)acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,4S,5R,6R)-2-(benzyloxy)-5-(^2H₃)acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: 5-(Acetylamino-d3)-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic Acid Benzyl Ether; N-Acetyl-2-O-benzyl-α-D-neuraminic Acid-d3

Database IDs

• PubChem SID: 162253300
• PubChem CID: 71312835

CALCULATED PROPERTIES

• Acid pKa: 3.1818042
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -3.490804
• LogD (pH = 7.4): -4.644947
• Log P: -1.1963379
• Molar Refractivity: 93.1452 cm^3
• Polarizability: 37.51837 Å^3
• Polar Surface Area: 165.78 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A170802

Labelled Neuraminic Acid derivative.