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

• ChemBase ID: 171175
• Molecular Formular: C27H35NO10
• Molecular Mass: 533.5675
• Monoisotopic Mass: 533.22609633
• SMILES: c1c(ccc(c1C(=O)CCc1ccccc1)OCC(CNCCC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)O
• Canonical SMILES: CCCNCC(O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)COc1ccc(cc1C(=O)CCc1ccccc1)O
• InChI: InChI=1S/C27H35NO10/c1-2-12-28-14-18(37-27-24(33)22(31)23(32)25(38-27)26(34)35)15-36-21-11-9-17(29)13-19(21)20(30)10-8-16-6-4-3-5-7-16/h3-7,9,11,13,18,22-25,27-29,31-33H,2,8,10,12,14-15H2,1H3,(H,34,35)/t18?,22-,23-,24+,25-,27+/m0/s1
• InChIKey: QGIYOVIZJDIKHE-UIITUPLWSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 164227085
• PubChem CID: 71749289

CALCULATED PROPERTIES

• Acid pKa: 2.9056134
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -0.6898686
• LogD (pH = 7.4): -0.69608563
• Log P: -0.6894396
• Molar Refractivity: 134.468 cm^3
• Polarizability: 53.54834 Å^3
• Polar Surface Area: 175.01 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H952437

A 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)