(2S,3S,4S,5R,6S)-6-[5-chloro-2-(2,4-dichlorophenoxy)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 178977
• Molecular Formular: C18H15Cl3O8
• Molecular Mass: 465.6659
• Monoisotopic Mass: 463.98325048
• SMILES: c1c(ccc(c1Cl)Oc1ccc(cc1O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)Cl)Cl
• Canonical SMILES: Clc1ccc(c(c1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)Oc1ccc(cc1Cl)Cl
• InChI: InChI=1S/C18H15Cl3O8/c19-7-1-3-10(9(21)5-7)27-11-4-2-8(20)6-12(11)28-18-15(24)13(22)14(23)16(29-18)17(25)26/h1-6,13-16,18,22-24H,(H,25,26)/t13-,14-,15+,16-,18+/m0/s1
• InChIKey: DNYVWBJVOYZRCX-RNGZQALNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[5-chloro-2-(2,4-dichlorophenoxy)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[5-chloro-2-(2,4-dichlorophenoxy)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 5-Chloro-2-(2,4-dichlorophenoxy)phenyl β-D-Glucopyranosiduronic Acid; Irgasan DP 300 Glucuronide; Triclosan O-β-D-Glucuronide

Database IDs

• CAS Number: 63156-12-7
• PubChem SID: 164234887
• PubChem CID: 71752714

CALCULATED PROPERTIES

• Acid pKa: 2.8807595
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.46439037
• LogD (pH = 7.4): -0.4528468
• Log P: 3.0343082
• Molar Refractivity: 100.7059 cm^3
• Polarizability: 40.7189 Å^3
• Polar Surface Area: 125.68 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T774260

Triclosan O-β-D-Glucuronide is a metabolite of the bacteriostat, Triclosan (T774250).

REFERENCES

• Moss, T. et al.: Food Chem. Toxicol., 38, 361 (2000)
• Wu, J. et al.: Sepu, 27, 724 (2000)