(2S,3S,4S,5R,6S)-6-[(2-{1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168805
• Molecular Formular: C23H29NO9
• Molecular Mass: 463.47766
• Monoisotopic Mass: 463.18423151
• SMILES: c12c3c([nH]c1c(ccc2)CC)C(OCC3)(CC)CC(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CCC1(OCCc2c1[nH]c1c2cccc1CC)CC(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H29NO9/c1-3-11-6-5-7-12-13-8-9-31-23(4-2,20(13)24-15(11)12)10-14(25)32-22-18(28)16(26)17(27)19(33-22)21(29)30/h5-7,16-19,22,24,26-28H,3-4,8-10H2,1-2H3,(H,29,30)/t16-,17-,18+,19-,22+,23?/m0/s1
• InChIKey: XJZNMEMKZBFUIZ-GWDFKZQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(2-{1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(2-{1,8-diethyl-3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetate) β-D-Glucopyranuronic Acid; Etodolac Glucuronide; rac Etodolac Acyl-β-D-glucuronide

Database IDs

• CAS Number: 79541-43-8
• PubChem SID: 162262937
• PubChem CID: 71316689

CALCULATED PROPERTIES

• Acid pKa: 3.1108735
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.8648117
• LogD (pH = 7.4): -1.9641266
• Log P: 1.4957329
• Molar Refractivity: 113.4559 cm^3
• Polarizability: 46.163177 Å^3
• Polar Surface Area: 158.54 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E933110

A metabolite of Etodolac (E933090).

REFERENCES

• Shapiro, R., et al.: J. Biol. Chem., 255, 3120 (1980)
• Faed, E., et al.: Drug Metab. Rev., 15, 1213 (1980)
• van Breemen, R., et al.: Drug Metab. Dispos., 13, 318 (1980)