(2R,3R,4R,5S,6R)-6-{2-[3-(4-{[(2,6-dimethylphenyl)carbamoyl]methyl}piperazin-1-yl)-2-hydroxypropoxy]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 166533
• Molecular Formular: C29H39N3O10
• Molecular Mass: 589.63406
• Monoisotopic Mass: 589.26354446
• SMILES: c1ccc(c(c1)OCC(CN1CCN(CC1)CC(=O)Nc1c(cccc1C)C)O)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(CN1CCN(CC1)CC(=O)Nc1c(C)cccc1C)COc1ccccc1O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C29H39N3O10/c1-17-6-5-7-18(2)23(17)30-22(34)15-32-12-10-31(11-13-32)14-19(33)16-40-20-8-3-4-9-21(20)41-29-26(37)24(35)25(36)27(42-29)28(38)39/h3-9,19,24-27,29,33,35-37H,10-16H2,1-2H3,(H,30,34)(H,38,39)/t19?,24-,25-,26+,27-,29+/m1/s1
• InChIKey: YLNYEZQRRIKMQF-GSGINOGSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-{2-[3-(4-{[(2,6-dimethylphenyl)carbamoyl]methyl}piperazin-1-yl)-2-hydroxypropoxy]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-{2-[3-(4-{[(2,6-dimethylphenyl)carbamoyl]methyl}piperazin-1-yl)-2-hydroxypropoxy]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-[3-[4-[2-[(2,6-Dimethylphenyl)amino]-2-oxoethyl]-1-piperazinyl]-2-hydroxypropoxy]phenyl β-D-Glucopyranosiduronic Acid; Desmethyl Ranolazine β-D-Glucuronide (mixture of diastereomers)

Database IDs

• CAS Number: 172300-93-5
• PubChem SID: 162260666
• PubChem CID: 71315764

CALCULATED PROPERTIES

• Acid pKa: 2.7831283
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -1.991203
• LogD (pH = 7.4): -2.3168857
• Log P: -1.9872854
• Molar Refractivity: 150.9899 cm^3
• Polarizability: 59.04161 Å^3
• Polar Surface Area: 181.49 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D292155

A metabolite of Ranolazine.

REFERENCES

• Chaitman, B.R., et al.: J. Am. Coll. Cardial., 43, 1375 (2004)
• McCormack, J.G., et al.: Gen. Pharmacol., 30, 639 (2004)
• Schofield, J.A.H., et al.: Expert Opin. Invest. Drugs, 11, 117 (2004)