(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-5-(4-methylbenzoyl)-3-nitrophenoxy]oxane-2-carboxylic acid

• ChemBase ID: 178700
• Molecular Formular: C20H19NO11
• Molecular Mass: 449.36496
• Monoisotopic Mass: 449.09581043
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)O)Oc1c(c(cc(c1)C(=O)c1ccc(cc1)C)[N+](=O)[O-])O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2cc(cc(c2O)[N+](=O)[O-])C(=O)c2ccc(cc2)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C20H19NO11/c1-8-2-4-9(5-3-8)13(22)10-6-11(21(29)30)14(23)12(7-10)31-20-17(26)15(24)16(25)18(32-20)19(27)28/h2-7,15-18,20,23-26H,1H3,(H,27,28)/t15-,16-,17+,18-,20+/m0/s1
• InChIKey: QQQCXCUCFPMHBX-HBWRTXEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-5-(4-methylbenzoyl)-3-nitrophenoxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-5-(4-methylbenzoyl)-3-nitrophenoxy]oxane-2-carboxylic acid
• Synonyms: 2-Hydroxy-5-(4-methylbenzoyl)-3-nitrophenyl β-D-Glucopyranosiduronic Acid; Ro 61-1448; Tolcapone 3-β-D-Glucuronide

Database IDs

• CAS Number: 204853-33-8
• PubChem SID: 164234610
• PubChem CID: 29987498

CALCULATED PROPERTIES

• Acid pKa: 2.386098
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -2.0102217
• LogD (pH = 7.4): -3.871468
• Log P: 1.3310802
• Molar Refractivity: 104.973 cm^3
• Polarizability: 40.599358 Å^3
• Polar Surface Area: 199.57 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T535260

A metabolite of Tolcapone (T535250).

REFERENCES

• Wikberg, T., et al.: Drug Metab. Dispos., 21, 81 (1993)
• Jorga, K., et al.: Clin. Pharmacol. Ther., 62, 300 (1993)
• Kurth, M., et al.: Neurology, 48, 81 (1993)