sodium (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(2R)-1-(naphthalen-1-yloxy)-3-[(propan-2-yl)amino]propan-2-yl]oxy}oxane-2-carboxylate

• ChemBase ID: 177025
• Molecular Formular: C22H28NNaO8
• Molecular Mass: 457.44939
• Monoisotopic Mass: 457.17126114
• SMILES: c1cccc2c1c(ccc2)OC[C@@H](CNC(C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-].[Na+]
• Canonical SMILES: CC(NC[C@@H](O[C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@@H]1O)O)O)COc1cccc2c1cccc2)C.[Na+]
• InChI: InChI=1S/C22H29NO8.Na/c1-12(2)23-10-14(11-29-16-9-5-7-13-6-3-4-8-15(13)16)30-22-19(26)17(24)18(25)20(31-22)21(27)28;/h3-9,12,14,17-20,22-26H,10-11H2,1-2H3,(H,27,28);/q;+1/p-1/t14-,17+,18+,19-,20+,22-;/m1./s1
• InChIKey: OSKYDLRSXKTYLZ-ABDGRLCTSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(2R)-1-(naphthalen-1-yloxy)-3-[(propan-2-yl)amino]propan-2-yl]oxy}oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(2R)-1-(isopropylamino)-3-(naphthalen-1-yloxy)propan-2-yl]oxy}oxane-2-carboxylate
• Synonyms: (R)-1-[[(1-Methylethyl)amino]methyl]-2-(1-naphthalenyloxy)ethyl β-D-Glucopyranosiduronic Acid Monosodium Salt; (+)-Propranolol Glucuronide Sodium; (R)-Propranolol Glucuronide Sodium; (R)-Propranolol β-D-Glucuronide Sodium Salt

Database IDs

• CAS Number: 87102-70-3
• PubChem SID: 164232935
• PubChem CID: 71751835

CALCULATED PROPERTIES

• Acid pKa: 3.026828
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.339562
• LogD (pH = 7.4): -1.3409661
• Log P: -1.3388066
• Molar Refractivity: 119.9435 cm^3
• Polarizability: 45.084633 Å^3
• Polar Surface Area: 140.54 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P831815

A metabolite of Propranolol (P831800). Antihypertensive; antianginal; antiarrhythmic (class II).

REFERENCES

• Reeves, P., et al.: Xenobiotica, 8, 313 (1978)
• Balon, K., et al.: Pharm. Res., 16, 882 (1978)
• Lange, R., et al.: Toxicol. Lett., 131, 97 (1978)