(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(4-hydroxyphenyl)(pyridin-2-yl)methyl]phenoxy}oxane-2-carboxylic acid

• ChemBase ID: 166099
• Molecular Formular: C24H23NO8
• Molecular Mass: 453.44132
• Monoisotopic Mass: 453.1423667
• SMILES: c1(C(c2ccc(cc2)O)c2ccccn2)ccc(cc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: Oc1ccc(cc1)C(c1ccccn1)c1ccc(cc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C24H23NO8/c26-15-8-4-13(5-9-15)18(17-3-1-2-12-25-17)14-6-10-16(11-7-14)32-24-21(29)19(27)20(28)22(33-24)23(30)31/h1-12,18-22,24,26-29H,(H,30,31)/t18?,19-,20-,21+,22-,24+/m0/s1
• InChIKey: RRVPDCNRRXUDQK-JZOWGYKDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(4-hydroxyphenyl)(pyridin-2-yl)methyl]phenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(4-hydroxyphenyl)(pyridin-2-yl)methyl]phenoxy}oxane-2-carboxylic acid
• Synonyms: 4-[(4-Hydroxyphenyl)-2-pyridinylmethyl]phenyl β-D-Glucopyranosiduronic Acid; α-(p-Hydroxyphenyl)-α-2-pyridyl-p-tolyl Glucosiduronic Acid; Desacetyl Bisacodyl β-D-Glucuronide

Database IDs

• CAS Number: 31050-47-2
• PubChem SID: 162260232
• PubChem CID: 71315565

CALCULATED PROPERTIES

• Acid pKa: 3.1719892
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.36551696
• LogD (pH = 7.4): -1.5868908
• Log P: 0.73478186
• Molar Refractivity: 113.8576 cm^3
• Polarizability: 45.11925 Å^3
• Polar Surface Area: 149.57 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D288650

The glucuronide metabolite of Desacetyl Bisacodyl (D288670).

REFERENCES

• Jauch, R., et al.: Arzneim.-Forsch., 27, 1045 (1977)
• Bradshaw, K., et al.: J. Pharm. Biomed. Anal., 13, 1355 (1977)
• Kudo,K., et al.: J. Anal. Toxocol., 22, 274 (1977)