(2S,3S,4S,5R,6S)-6-{5-[(1E)-2-cyano-2-(diethylcarbamoyl)eth-1-en-1-yl]-2-hydroxy-3-nitrophenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 167931
• Molecular Formular: C20H23N3O11
• Molecular Mass: 481.41012
• Monoisotopic Mass: 481.13325857
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)O)Oc1c(c(cc(c1)/C=C(/C(=O)N(CC)CC)\C#N)[N+](=O)[O-])O)O)O)O
• Canonical SMILES: CCN(C(=O)/C(=C/c1cc(O[C@@H]2O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]2O)O)O)c(c(c1)[N+](=O)[O-])O)/C#N)CC
• InChI: InChI=1S/C20H23N3O11/c1-3-22(4-2)18(28)10(8-21)5-9-6-11(23(31)32)13(24)12(7-9)33-20-16(27)14(25)15(26)17(34-20)19(29)30/h5-7,14-17,20,24-27H,3-4H2,1-2H3,(H,29,30)/b10-5+/t14-,15-,16+,17-,20+/m0/s1
• InChIKey: QFIJKZUWSRMQEH-IJKJBMBDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{5-[(1E)-2-cyano-2-(diethylcarbamoyl)eth-1-en-1-yl]-2-hydroxy-3-nitrophenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{5-[(1E)-2-cyano-2-(diethylcarbamoyl)eth-1-en-1-yl]-2-hydroxy-3-nitrophenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 5-[(1E)-2-Cyano-3-(diethylamino)-3-oxo-1-propenyl]-2-hydroxy-3-nitrophenyl β-D-Glucopyranosiduronic Acid; Entacapone 3-β-D-Glucuronide

Database IDs

• CAS Number: 158-69-75-1
• PubChem SID: 162262064
• PubChem CID: 29979332

CALCULATED PROPERTIES

• Acid pKa: 2.5814428
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -3.2880497
• LogD (pH = 7.4): -5.2238126
• Log P: -0.3129697
• Molar Refractivity: 112.5246 cm^3
• Polarizability: 42.903873 Å^3
• Polar Surface Area: 226.6 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E558510

The main metabolite of Entacapone and Tolcapone.

REFERENCES

• Mannisto, P., et al.: Prog. Drug Res., 39, 291(1992)
• Nishi, H., et al.: J. Pharm. Biomed. Anal., 11, 1277 (1992)
• Wikberg, T., et al.: Eur. J. Drug Metab. Pharmacokinet., 18, 359 (1992)