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

• ChemBase ID: 171205
• Molecular Formular: C22H29NO9
• Molecular Mass: 451.46696
• Monoisotopic Mass: 451.18423151
• SMILES: c1ccc2c(c1)c(ccc2O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)O)OCC(CNC(C)C)O
• Canonical SMILES: OC(COc1ccc(c2c1cccc2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)CNC(C)C
• InChI: InChI=1S/C22H29NO9/c1-11(2)23-9-12(24)10-30-15-7-8-16(14-6-4-3-5-13(14)15)31-22-19(27)17(25)18(26)20(32-22)21(28)29/h3-8,11-12,17-20,22-27H,9-10H2,1-2H3,(H,28,29)/t12?,17-,18-,19+,20-,22+/m0/s1
• InChIKey: GCESUDQAKCEBSY-MBOKBCRSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}naphthalen-1-yl)oxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({4-[2-hydroxy-3-(isopropylamino)propoxy]naphthalen-1-yl}oxy)oxane-2-carboxylic acid
• Synonyms: 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenyl β-D-glucopyranosiduronic Acid; 4-Hydroxy Propranolol β-D-Glucuronide (Mixture of Diastereomers)

Database IDs

• CAS Number: 94731-13-2
• PubChem SID: 164227115
• PubChem CID: 125231

CALCULATED PROPERTIES

• Acid pKa: 3.036286
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -2.1403863
• LogD (pH = 7.4): -2.1412852
• Log P: -2.1395996
• Molar Refractivity: 110.8184 cm^3
• Polarizability: 45.835316 Å^3
• Polar Surface Area: 157.94 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Beige Solid
• Melting Point: 175-177°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H952535

A metabolite of 4-Hydroxy propranolol. Antihypertensive; antianginal; antiarrhythmic (class II).

REFERENCES

• Walle, T., et al.: Clin. Pharmacol. Ther., 46, 257 (1989)
• Christ, D.D., et al.: Drug Metab. Dispos., 18, 1 (1989)