(5S)-2,5-dihydroxy-6-(hydroxymethyl)(2-13C)oxan-3-one

• ChemBase ID: 165965
• Molecular Formular: C6H10O5
• Molecular Mass: 163.13325484
• Monoisotopic Mass: 163.05617826
• SMILES: [C@@H]1(CC(=O)[13CH](OC1CO)O)O
• Canonical SMILES: OCC1O[13CH](O)C(=O)C[C@@H]1O
• InChI: InChI=1S/C6H10O5/c7-2-5-3(8)1-4(9)6(10)11-5/h3,5-8,10H,1-2H2/t3-,5?,6?/m0/s1/i6+1
• InChIKey: UHPMJDGOAZMIID-GLGOFWJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-2,5-dihydroxy-6-(hydroxymethyl)(2-^1^3C)oxan-3-one
• IUPAC Traditional name: (5S)-2,5-dihydroxy-6-(hydroxymethyl)(2-^1^3C)oxan-3-one
• Synonyms: 3-Deoxy-D-erythro-hexulose-13C; 2-Keto-3-Deoxyglucose-13C; D-3-Deoxyglucosone-13C; 3-Deoxy-D-erythro-hexos-2-ulose-13C; 3DG-13C; 3-Deoxy-D-glucosone-13C; 3-Deoxyglucosone-13C

Database IDs

• PubChem SID: 162260098
• PubChem CID: 71315481

CALCULATED PROPERTIES

• Acid pKa: 10.440278
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.6789145
• LogD (pH = 7.4): -1.6793048
• Log P: -1.6789095
• Molar Refractivity: 33.9119 cm^3
• Polarizability: 13.910811 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D239152

Labelled 3-Deoxyglucosone (D239150). An intermediate in the Maillard reaction of proteins with glucose, which is metabolised to 3-Deoxyfructose. An intermediate in the formation of pyrraline, which might contribute to a pathological effect, such as carci

REFERENCES

• Kato, H. et al.: Agric. Biol. Chem., 51, 683 (1987)
• Hayase, F. et al.: J. Biol. Chem., 264, 3758 (1987)
• Kato, H. et al.: Biochimica et Biophysica Acta, 1035, 71 (1990)