(2S,3S,4S,5R,6S)-6-({1-[(3,4-dimethoxyphenyl)methyl]-7-methoxyisoquinolin-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 165800
• Molecular Formular: C25H27NO10
• Molecular Mass: 501.48258
• Monoisotopic Mass: 501.16349607
• SMILES: O1[C@H]([C@H]([C@H]([C@@H]([C@@H]1C(=O)O)O)O)O)Oc1cc2c(cc1OC)c(ncc2)Cc1ccc(c(c1)OC)OC
• Canonical SMILES: COc1cc2c(nccc2cc1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)Cc1ccc(c(c1)OC)OC
• InChI: InChI=1S/C25H27NO10/c1-32-16-5-4-12(9-17(16)33-2)8-15-14-11-18(34-3)19(10-13(14)6-7-26-15)35-25-22(29)20(27)21(28)23(36-25)24(30)31/h4-7,9-11,20-23,25,27-29H,8H2,1-3H3,(H,30,31)/t20-,21-,22+,23-,25+/m0/s1
• InChIKey: UGQMKGSZOXHZOP-LYVDORBWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({1-[(3,4-dimethoxyphenyl)methyl]-7-methoxyisoquinolin-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({1-[(3,4-dimethoxyphenyl)methyl]-7-methoxyisoquinolin-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 6-Demethyl Papaverine β-D-Glucuronide

Database IDs

• PubChem SID: 162259933
• PubChem CID: 71315398

CALCULATED PROPERTIES

• Acid pKa: 3.1557653
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -0.81378436
• LogD (pH = 7.4): -2.0604591
• Log P: -0.63040036
• Molar Refractivity: 123.047 cm^3
• Polarizability: 49.99827 Å^3
• Polar Surface Area: 157.03 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 154-159°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D231210

A metabolite of Papaverine (P190500).

REFERENCES

• Belpaire, F.M., et al.: Xenobiotica, 8, 297 (1978)