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

• ChemBase ID: 160651
• Molecular Formular: C9H14O8
• Molecular Mass: 250.20266
• Monoisotopic Mass: 250.06886741
• SMILES: [C@@H]1([C@@H]([C@@H](C=C(O1)C(=O)O)O)O)[C@@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1OC(=C[C@H]([C@H]1O)O)C(=O)O)O)O
• InChI: InChI=1S/C9H14O8/c10-2-4(12)7(14)8-6(13)3(11)1-5(17-8)9(15)16/h1,3-4,6-8,10-14H,2H2,(H,15,16)/t3-,4+,6+,7+,8+/m0/s1
• InChIKey: IZHMZNLAOQHCDZ-LRGKAINGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S)-3,4-dihydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• IUPAC Traditional name: (4S,5R,6R)-4,5-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-5,6-dihydro-4H-pyran-2-carboxylic acid
• Synonyms: 2,6-Anhydro-3-deoxy-D-glycero-D-galacto-non-2-enoic Acid; Kdn2en, 2,3-Dehydro-2-deoxy-Kdn

Database IDs

• CAS Number: 188854-96-8
• PubChem SID: 162254786
• PubChem CID: 11021292

CALCULATED PROPERTIES

• Acid pKa: 3.4031184
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -5.52237
• LogD (pH = 7.4): -6.81186
• Log P: -3.400117
• Molar Refractivity: 53.0094 cm^3
• Polarizability: 21.040075 Å^3
• Polar Surface Area: 147.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Amorphous Powder

DETAILS

Toronto Research Chemicals - A637750

A potential inhibitor of virus sialidase.

REFERENCES

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