sodium (2S,3S,4S,5R,6S)-6-[4-(2H3)acetamidophenoxy]-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 158937
• Molecular Formular: C14H16NNaO8
• Molecular Mass: 349.26851
• Monoisotopic Mass: 349.07736076
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)[O-])Oc1ccc(cc1)NC(=O)C)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-(^2H₃)acetamidophenoxy]-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6S)-6-[4-(^2H₃)acetamidophenoxy]-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: Acetaminophen Glucuronide-d3 Sodium Salt, Paracetamol Glucuronide-d3 sodium salt; 4-Acetamidophenyl β-D-Glucuronide-d3 Sodium Salt

Database IDs

• PubChem SID: 162253072
• PubChem CID: 71312745

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: 29.42302 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: White to Off-White Solid
• Melting Point: 214-216°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A158502

The major urinary Labelled metabolite of acetaminophen in man.

REFERENCES

• Bales et. al., Clinical Chemistry, 30 (10)
• 1631 (1984)