(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S)-2-(6-methoxynaphthalen-2-yl)propanoyl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 174990
• Molecular Formular: C20H22O9
• Molecular Mass: 406.38328
• Monoisotopic Mass: 406.12638228
• SMILES: c1c2c(ccc1[C@@H](C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C)cc(cc2)OC
• Canonical SMILES: COc1ccc2c(c1)ccc(c2)[C@@H](C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C20H22O9/c1-9(10-3-4-12-8-13(27-2)6-5-11(12)7-10)19(26)29-20-16(23)14(21)15(22)17(28-20)18(24)25/h3-9,14-17,20-23H,1-2H3,(H,24,25)/t9-,14-,15-,16+,17-,20-/m0/s1
• InChIKey: XRHIELLXTVJOKM-ODXKUVGNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S)-2-(6-methoxynaphthalen-2-yl)propanoyl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S)-2-(6-methoxynaphthalen-2-yl)propanoyl]oxy}oxane-2-carboxylic acid
• Synonyms: 4-[(αS)-6-methoxy-α-methyl-2-naphthaleneacetate] β-D-Glucopyranuronic Acid; Naproxen Iso-acyl Glucuronide; (S)-Naproxen Iso-acyl-β-D-glucuronideDISCONTINUED

Database IDs

• CAS Number: 219476-92-3
• PubChem SID: 164230900
• PubChem CID: 181715

CALCULATED PROPERTIES

• Acid pKa: 3.43552
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.0155784
• LogD (pH = 7.4): -2.3556743
• Log P: 1.0379924
• Molar Refractivity: 97.1521 cm^3
• Polarizability: 40.11152 Å^3
• Polar Surface Area: 142.75 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N377540

A metabolite of Naproxen. The 4-O-acyl glucuronide (4-isomer) of (S)-Naproxen (isoNAG).

REFERENCES

• Runkel, R., et al.: J. Pharmaceut. Sci., 61, 703 (1972)
• Ding, A., et al.: Drug Metab. Dispos., 23, 369 (1972)
• Lo, A., et al.: Xenobiotica, 31, 309 (1972)