(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-({1-[2-(3-phenylpropanoyl)phenoxy]-3-{[(2,2,3,3,3-2H5)propyl]amino}propan-2-yl}oxy)oxane-2-carboxylic acid

• ChemBase ID: 176987
• Molecular Formular: C27H35NO9
• Molecular Mass: 517.5681
• Monoisotopic Mass: 517.23118171
• SMILES: c1cccc(c1C(=O)CCc1ccccc1)OCC(CNCCC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CCCNCC(O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)COc1ccccc1C(=O)CCc1ccccc1
• InChI: InChI=1S/C27H35NO9/c1-2-14-28-15-18(36-27-24(32)22(30)23(31)25(37-27)26(33)34)16-35-21-11-7-6-10-19(21)20(29)13-12-17-8-4-3-5-9-17/h3-11,18,22-25,27-28,30-32H,2,12-16H2,1H3,(H,33,34)/t18?,22-,23-,24+,25-,27+/m0/s1
• InChIKey: DPSCUTCAFODJSS-UIITUPLWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-({1-[2-(3-phenylpropanoyl)phenoxy]-3-{[(2,2,3,3,3-^2H₅)propyl]amino}propan-2-yl}oxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-({1-[2-(3-phenylpropanoyl)phenoxy]-3-[(2,2,3,3,3-^2H₅)propylamino]propan-2-yl}oxy)oxane-2-carboxylic acid
• Synonyms: 1-[2-[2-β-D-Glucopyranuronosyl-3-(propylamino-d5)propoxy]phenyl]-3-phenyl-1-propanone; 1-[2-[3-(Propylamino-d5)propoxy]phenyl]-3-phenyl-1-propanone Glucuronide; Propafenone-d5 β-D-Glucuronide

Database IDs

• PubChem SID: 164232897
• PubChem CID: 71751811

CALCULATED PROPERTIES

• Acid pKa: 2.9133403
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -0.38626608
• LogD (pH = 7.4): -0.3880994
• Log P: -0.38570482
• Molar Refractivity: 132.4871 cm^3
• Polarizability: 52.904655 Å^3
• Polar Surface Area: 154.78 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P757512

A labelled metabolite of Propafenone (P757495). Used in kinetic and pharmacological studies in man and animal.

REFERENCES

• Bryson, H. M., et al.:Drugs, 45, 85 (1993)
• Hollmann, M., et al.: Arzneim.-Forsch., 33, 763 (1993)
• Neidlein, R. et al: Arzneim.-Forsch., 38, 1257 (1993)
• Rae, A. P., et al.: Am. J. Cardiol., 82, 59N (1998)