prop-2-en-1-yl (3S,4S)-3,4,5,6-tetrahydroxy(2,3,4,5,6-13C5)oxane-2-carboxylate

• ChemBase ID: 159690
• Molecular Formular: C9H14O7
• Molecular Mass: 240.15918903
• Monoisotopic Mass: 240.09408182
• SMILES: [13C@@H]1([13C@@H]([13CH]([13CH](O[13CH]1[13C](=O)OCC=C)O)O)O)O
• Canonical SMILES: C=CCO[13C](=O)[13CH]1O[13CH](O)[13CH]([13C@H]([13C@@H]1O)O)O
• InChI: InChI=1S/C9H14O7/c1-2-3-15-9(14)7-5(11)4(10)6(12)8(13)16-7/h2,4-8,10-13H,1,3H2/t4-,5-,6?,7?,8?/m0/s1/i4+1,5+1,6+1,7+1,8+1,9+1
• InChIKey: HYPHSXHTCHCXAT-ZQSLFJNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-en-1-yl (3S,4S)-3,4,5,6-tetrahydroxy(2,3,4,5,6-^1^3C₅)oxane-2-carboxylate
• IUPAC Traditional name: prop-2-en-1-yl (3S,4S)-3,4,5,6-tetrahydroxy(2,3,4,5,6-^1^3C₅)oxane-2-carboxylate
• Synonyms: D-Glucopyranuronic Acid-13C6 2-Propen-1-yl Ester; D-Glucuronic Acid-13C6 2-Propenyl Ester; Allyl D-Glucuronate-13C6

Database IDs

• PubChem SID: 162253825
• PubChem CID: 71313092

CALCULATED PROPERTIES

• Acid pKa: 11.283208
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.7351215
• LogD (pH = 7.4): -1.7351775
• Log P: -1.7351208
• Molar Refractivity: 49.7226 cm^3
• Polarizability: 20.550245 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol
• Apperance: White Solid
• Melting Point: 111-113°C

Safety Information

• Storage Condition: -86°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A555402

Labelled Allyl D-Glucuronate. It is used in efficient synthesis of 1β-O-acyl glucuronides via regioselective acylation of allyl or benzyl D-glucuronate. Αcyl glucuronides are known metabolites of important drugs.

REFERENCES

• Kaspersen, F., et al.: Xenobiotica, 17, 1451 (1987)
• Ebner, T., et al.: Drug Metab. Dispos., 27, 1143 (1987)
• Shipkova, M., et al.: Ther. Drug Monit., 25, 1 (1987)
• Stachulski, A., et al.: J. Med. Chem., 49, 6931 (1987)