(2S,3S,4S,5R,6S)-6-{2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 170914
• Molecular Formular: C28H39NO8
• Molecular Mass: 517.61116
• Monoisotopic Mass: 517.26756721
• SMILES: c1c(c(cc(c1)CO)[C@H](CCN(C(C)C)C(C)C)c1ccccc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OCc1ccc(c(c1)[C@@H](c1ccccc1)CCN(C(C)C)C(C)C)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C28H39NO8/c1-16(2)29(17(3)4)13-12-20(19-8-6-5-7-9-19)21-14-18(15-30)10-11-22(21)36-28-25(33)23(31)24(32)26(37-28)27(34)35/h5-11,14,16-17,20,23-26,28,30-33H,12-13,15H2,1-4H3,(H,34,35)/t20-,23+,24+,25-,26+,28-/m1/s1
• InChIKey: NTDPQHVAFNCNKD-GYQAOLNFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-[(1R)-3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl β-D-Glucopyranosiduronic Acid; 5-Hydroxymethyl Tolterodine β-D-Glucuronide

Database IDs

• CAS Number: 210573-52-7
• PubChem SID: 164226824
• PubChem CID: 71749184

CALCULATED PROPERTIES

• Acid pKa: 2.9734843
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.13517694
• LogD (pH = 7.4): -0.13432537
• Log P: -0.13422027
• Molar Refractivity: 137.7437 cm^3
• Polarizability: 54.494194 Å^3
• Polar Surface Area: 139.92 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H948368

A metabolite of Tolterodine (T535795).

REFERENCES

• Lowry, O., et al.: J. Biol. Chem., 193, 265 (1951)
• Andersson, K., et al.: Drugs, 35, 477 (1951)
• Shimada, T., et al.: J. Pharmacol. Exp. Ther., 270, 414 (1951)
• Postlind, H, et al.: Drug Metab. Disp., 26, 289 (1951)