(5S)-3-methylidene-5-[(1S,2S,3R,4R)-1,2,3,4,5-pentahydroxypentyl]oxolan-2-one

• ChemBase ID: 167224
• Molecular Formular: C10H16O7
• Molecular Mass: 248.22984
• Monoisotopic Mass: 248.08960285
• SMILES: C1(=O)C(=C)C[C@H](O1)[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]([C@@H]([C@H]1OC(=O)C(=C)C1)O)O)O)O
• InChI: InChI=1S/C10H16O7/c1-4-2-6(17-10(4)16)8(14)9(15)7(13)5(12)3-11/h5-9,11-15H,1-3H2/t5-,6+,7-,8-,9+/m1/s1
• InChIKey: UMKGNATWHHYUEM-WUNNTHRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-3-methylidene-5-[(1S,2S,3R,4R)-1,2,3,4,5-pentahydroxypentyl]oxolan-2-one
• IUPAC Traditional name: (5S)-3-methylidene-5-[(1S,2S,3R,4R)-1,2,3,4,5-pentahydroxypentyl]oxolan-2-one
• Synonyms: 2,3-Dideoxy-2-methylene-D-glycero-D-galacto-nononic Acid γ-Lactone

Database IDs

• CAS Number: 289697-66-1
• PubChem SID: 162261357
• PubChem CID: 11436576

CALCULATED PROPERTIES

• Acid pKa: 12.531444
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.3174825
• LogD (pH = 7.4): -2.3174856
• Log P: -2.3174825
• Molar Refractivity: 54.4985 cm^3
• Polarizability: 22.290997 Å^3
• Polar Surface Area: 127.45 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D440955

Intermediate for the synthesis of KDN and other sialic acids.

REFERENCES

• Nadano, D., et al.: J. Biol. Chem., 261, 11550 (1986)
• Livingston, B., et al.: J. Biol. Chem. 263, 9443 (1988).