(2S,3S,4S,5R,6R)-6-(5-ethyl-2,4,6-trioxo-5-phenyl-1,3-diazinan-1-yl)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 176485
• Molecular Formular: C18H20N2O9
• Molecular Mass: 408.3594
• Monoisotopic Mass: 408.11688023
• SMILES: C1(=O)N(C(=O)NC(=O)C1(c1ccccc1)CC)[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CCC1(C(=O)NC(=O)N(C1=O)[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)c1ccccc1
• InChI: InChI=1S/C18H20N2O9/c1-2-18(8-6-4-3-5-7-8)15(26)19-17(28)20(16(18)27)13-11(23)9(21)10(22)12(29-13)14(24)25/h3-7,9-13,21-23H,2H2,1H3,(H,24,25)(H,19,26,28)/t9-,10-,11+,12-,13+,18?/m0/s1
• InChIKey: QMKGHGCGTFFYNT-OGKJXGCJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-(5-ethyl-2,4,6-trioxo-5-phenyl-1,3-diazinan-1-yl)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-(5-ethyl-2,4,6-trioxo-5-phenyl-1,3-diazinan-1-yl)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-Deoxy-1-(5-ethyltetrahydro-2,4,6-trioxo-5-phenyl-1(2H)-pyrimidinyl)-β-D-glucopyranuronic Acid; Phenobarbital N-β-D-Glucuronide

Database IDs

• CAS Number: 1031858-68-0
• PubChem SID: 164232395
• PubChem CID: 71751583

CALCULATED PROPERTIES

• Acid pKa: 3.3246813
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.623723
• LogD (pH = 7.4): -3.9323256
• Log P: -0.46368143
• Molar Refractivity: 92.1725 cm^3
• Polarizability: 36.852097 Å^3
• Polar Surface Area: 173.7 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P316770

A metabolite of Phenobarbital (P316760).

REFERENCES

• Soine, W.H., et al.: Drug Metab. Dispos., 12, 792 (1984)
• Soine, W.H., et al.: J. Pharmac. Sci., 80, 99 (1984)