sodium (2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 133827
• Molecular Formular: C14H16NNaO8
• Molecular Mass: 349.26851
• Monoisotopic Mass: 349.07736076
• SMILES: CC(=O)Nc1ccc(cc1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)[O-])O)O)O.[Na+]
• Canonical SMILES: CC(=O)Nc1ccc(cc1)O[C@@H]1O[C@H](C(=O)[O-])[C@H]([C@@H]([C@H]1O)O)O.[Na+]
• InChI: InChI=1S/C14H17NO8.Na/c1-6(16)15-7-2-4-8(5-3-7)22-14-11(19)9(17)10(18)12(23-14)13(20)21;/h2-5,9-12,14,17-19H,1H3,(H,15,16)(H,20,21);/q;+1/p-1/t9-,10-,11+,12-,14+;/m0./s1
• InChIKey: OINXIJJEOMGKPB-CYRSAHDMSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: Acetaminophen glucuronide; Paracetamol glucuronide; p-Acetamidophenyl β-D-glucuronide sodium salt; Acetaminophen Glucuronide Sodium Salt; Paracetamol Glucuronide Sodium Salt; 4-Acetamidophenyl β-D-Glucuronide Sodium Salt

Database IDs

• CAS Number: 120595-80-4
• MDL Number: MFCD00153898
• PubChem SID: 24890866; 162228104
• PubChem CID: 23677081

CALCULATED PROPERTIES

• Acid pKa: 3.16535
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.3501763
• LogD (pH = 7.4): -4.4917502
• Log P: -1.0404027
• Molar Refractivity: 85.7508 cm^3
• Polarizability: 29.422882 Å^3
• Polar Surface Area: 148.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 232-233°C (dec)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - A4438

Application
Acetaminophen glucuronide (AA-Gluc) is used as a reference material in procedures that analyse urine and plasma for acetaminophen metabolites to indicate hepatotoxicity.

Toronto Research Chemicals - A158500

The major urinary metabolite of Acetaminophen (A161220) (Paracetamol) in man.

REFERENCES

• Bales, et al.: Clinical Chemistry, 30, 1631 (1984)