methyl (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-carboxylate

• ChemBase ID: 171200
• Molecular Formular: C23H31NO9
• Molecular Mass: 465.49354
• Monoisotopic Mass: 465.19988158
• SMILES: c1ccc2c(c1)c(ccc2O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)OC)OCC(CNC(C)C)O
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc(c3c2cccc3)OCC(CNC(C)C)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H31NO9/c1-12(2)24-10-13(25)11-31-16-8-9-17(15-7-5-4-6-14(15)16)32-23-20(28)18(26)19(27)21(33-23)22(29)30-3/h4-9,12-13,18-21,23-28H,10-11H2,1-3H3/t13?,18-,19-,20+,21-,23+/m0/s1
• InChIKey: DXYKRIFMHUJPBT-NHTXKFPZSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 164227110
• PubChem CID: 71749299

CALCULATED PROPERTIES

• Acid pKa: 12.161719
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.714999
• LogD (pH = 7.4): -1.7470006
• Log P: 0.4782311
• Molar Refractivity: 115.5875 cm^3
• Polarizability: 47.913548 Å^3
• Polar Surface Area: 146.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethylformamide; DMSO; Methanol
• Apperance: Light-Brown Solid

DETAILS

Toronto Research Chemicals - H952520

Protected 4-Hydroxy Propranolol metabolite.