(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2,2,2-trichloroethoxy)oxane-2-carboxylic acid

• ChemBase ID: 178947
• Molecular Formular: C8H11Cl3O7
• Molecular Mass: 325.52774
• Monoisotopic Mass: 323.95703573
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)O)OCC(Cl)(Cl)Cl)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OCC(Cl)(Cl)Cl)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C8H11Cl3O7/c9-8(10,11)1-17-7-4(14)2(12)3(13)5(18-7)6(15)16/h2-5,7,12-14H,1H2,(H,15,16)/t2-,3-,4+,5-,7+/m0/s1
• InChIKey: IQOASJJGUQMXDW-GHQVIJFQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2,2,2-trichloroethoxy)oxane-2-carboxylic acid
• IUPAC Traditional name: trichloroethanol glucuronide
• Synonyms: 2,2,2-Trichloroethyl β-D-Glucopyranosiduronic Acid; 2,2,2-Trichloroethanol Glucuronide; Urochloralic Acid; β,β,β-Trichloroethyl-β-D-glucuronic Acid; Trichloroethyl β-D-Glucuronide

Database IDs

• CAS Number: 97-25-6
• PubChem SID: 164234857
• PubChem CID: 3036914

CALCULATED PROPERTIES

• Acid pKa: 3.2138412
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.6582634
• LogD (pH = 7.4): -3.8369648
• Log P: -0.39398214
• Molar Refractivity: 60.4965 cm^3
• Polarizability: 24.750532 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White to Pale Pink Solid
• Melting Point: 72-77°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T774110

A metabolite of chloral hydrate (CH) and trichloroethylene (TRI).

REFERENCES

• Salmon, A., et al.: Clin. Toxicol., 33, 115 (1995)
• Xu, G., et al.: Drug Metab. Dispos., 23, 1412 (1995)
• Bull, R., et al.: Toxicol. Appl. Pharmacol., 182, 55 (1995)