(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(naphthalen-1-yloxy)oxane-2-carboxylic acid

• ChemBase ID: 174969
• Molecular Formular: C16H16O7
• Molecular Mass: 320.29404
• Monoisotopic Mass: 320.08960285
• SMILES: c1ccc2c(c1O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)cccc2
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2cccc3c2cccc3)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H16O7/c17-11-12(18)14(15(20)21)23-16(13(11)19)22-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11-14,16-19H,(H,20,21)/t11-,12-,13+,14-,16+/m0/s1
• InChIKey: KEQWBZWOGRCILF-JHZZJYKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(naphthalen-1-yloxy)oxane-2-carboxylic acid
• IUPAC Traditional name: naphthyl glucuronide
• Synonyms: 1-Naphthalenyl β-D-Glucopyranosiduronic Acid; α-Naphthol Glucuronide; α-Naphthyl β-D-Glucuronide; α-Naphthyl β-Glucuronide; 1-Naphthyl Glucosiduronic Acid; 1-Naphthol β-D-Glucuronide

Database IDs

• CAS Number: 17238-47-0
• PubChem SID: 164230879
• PubChem CID: 114851

CALCULATED PROPERTIES

• Acid pKa: 3.5694904
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.213413
• LogD (pH = 7.4): -2.6420875
• Log P: 0.7113637
• Molar Refractivity: 76.5009 cm^3
• Polarizability: 31.94348 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 100-106°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - N368000

A metabolite of 1-Naphthol.

REFERENCES

• Redegeld, F., et al.: J. Pharmacol. Exp. Ther., 244, 263 (1988)
• Lohr, J., et al.: Pharmacol. Rev., 50, 107 (1988)
• Yokota, H., et al.: Biochem. J., 340, 405 (1988)
• Daidoji, T., et al.: Drug Metab. Dispos., 31, 993 (1988)