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

• ChemBase ID: 159724
• Molecular Formular: C9H15NO7
• Molecular Mass: 249.2179
• Monoisotopic Mass: 249.08485183
• SMILES: [C@@H]1([C@@H]([C@@H](C=C(O1)C(=O)O)N)O)[C@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@@H]([C@@H]1OC(=C[C@H]([C@H]1O)N)C(=O)O)O)O
• InChI: InChI=1S/C9H15NO7/c10-3-1-5(9(15)16)17-8(6(3)13)7(14)4(12)2-11/h1,3-4,6-8,11-14H,2,10H2,(H,15,16)/t3-,4+,6+,7+,8+/m0/s1
• InChIKey: DLPBPEUAQGGZEN-LRGKAINGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S)-4-amino-3-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• IUPAC Traditional name: (4S,5R,6R)-4-amino-5-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-5,6-dihydro-4H-pyran-2-carboxylic acid
• Synonyms: 4-Amino-Kdn2en; 4-Amino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-non-2-enoic Acid

Database IDs

• CAS Number: 263155-12-0
• PubChem SID: 162253859
• PubChem CID: 10999418

CALCULATED PROPERTIES

• Acid pKa: 3.2133412
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -5.771463
• LogD (pH = 7.4): -5.783695
• Log P: -5.7705746
• Molar Refractivity: 54.6669 cm^3
• Polarizability: 21.84451 Å^3
• Polar Surface Area: 153.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Amorphous Powder

DETAILS

Toronto Research Chemicals - A583150

A potential inhibitor of virus sialidase.

REFERENCES

• Sun, X-L, et al.: Carbohydrate Research, 323, 1 (2000)