methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[4-(2H3)acetamidophenoxy]oxane-2-carboxylate

• ChemBase ID: 158940
• Molecular Formular: C21H25NO11
• Molecular Mass: 467.4233
• Monoisotopic Mass: 467.14276063
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)OC)Oc1ccc(cc1)NC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)NC(=O)C)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C21H25NO11/c1-10(23)22-14-6-8-15(9-7-14)32-21-19(31-13(4)26)17(30-12(3)25)16(29-11(2)24)18(33-21)20(27)28-5/h6-9,16-19,21H,1-5H3,(H,22,23)/t16-,17-,18-,19+,21+/m0/s1
• InChIKey: CGFRFKWGBUUPFU-VDRZXAFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[4-(^2H₃)acetamidophenoxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[4-(^2H₃)acetamidophenoxy]oxane-2-carboxylate
• Synonyms: 4-(Acetylamino)phenyl-d3 β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate; p-Acetamidophenyl-d3 β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate; 4-Acetamidophenyl-d3-2,3,4-tri-O-acetyl-β-D-glucuronide, Methyl Ester

Database IDs

• PubChem SID: 162253075
• PubChem CID: 71312747

CALCULATED PROPERTIES

• Acid pKa: 14.8745365
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.42886758
• LogD (pH = 7.4): 0.42886758
• Log P: 0.42886758
• Molar Refractivity: 107.1373 cm^3
• Polarizability: 43.159443 Å^3
• Polar Surface Area: 152.76 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Pale-Yellow Solid

DETAILS

Toronto Research Chemicals - A161187

Intermediate in the preparation of labelled Acetaminophen metabolites

REFERENCES

• Calder, I., et al.: J. Med. Chem., 24, 988 (1981)
• Iino, N., et al.: Chem. Pharm. Bull., 40, 1852 (1981)