(2S,3S,4S,5R,6S)-6-(4-aminophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 160409
• Molecular Formular: C12H15NO7
• Molecular Mass: 285.25
• Monoisotopic Mass: 285.08485183
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)O)Oc1ccc(cc1)N)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)N)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H15NO7/c13-5-1-3-6(4-2-5)19-12-9(16)7(14)8(15)10(20-12)11(17)18/h1-4,7-10,12,14-16H,13H2,(H,17,18)/t7-,8-,9+,10-,12+/m0/s1
• InChIKey: ZARKEMJKQOXOSQ-GOVZDWNOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-(4-aminophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-(4-aminophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4-Aminophenyl β-D-Glucopyranosiduronic Acid; 4-Aminophenyl β-D-Glucuronide

Database IDs

• CAS Number: 21080-66-0
• PubChem SID: 162254544
• PubChem CID: 20598909

CALCULATED PROPERTIES

• Acid pKa: 3.2618086
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -3.078474
• LogD (pH = 7.4): -4.454895
• Log P: -2.3906593
• Molar Refractivity: 64.7511 cm^3
• Polarizability: 25.76496 Å^3
• Polar Surface Area: 142.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Hot Methanol; Water
• Apperance: Beige to Yellow Solid
• Melting Point: >180°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A624010

Metabolite of p-Aminophenol

REFERENCES

• Yan, Z., et al.: Drug Metab. Disposition, 28, 880 (2000)
• Nohynek, G., et al.: Toxicol. Lett., 158, 196 (2000)