(2S,3S,4S,5R,6S)-6-{[6-(2H11)cyclohexyl-4-methyl-2-oxo-1,2-dihydropyridin-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 164752
• Molecular Formular: C18H25NO8
• Molecular Mass: 383.393
• Monoisotopic Mass: 383.15801677
• SMILES: O([C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)O)n1c(cc(cc1=O)C)C1CCCCC1
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](On2c(=O)cc(cc2C2CCCCC2)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C18H25NO8/c1-9-7-11(10-5-3-2-4-6-10)19(12(20)8-9)27-18-15(23)13(21)14(22)16(26-18)17(24)25/h7-8,10,13-16,18,21-23H,2-6H2,1H3,(H,24,25)/t13-,14-,15+,16-,18-/m0/s1
• InChIKey: RRBPTSPRUYTJLL-RPUYLAQPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[6-(^2H₁₁)cyclohexyl-4-methyl-2-oxo-1,2-dihydropyridin-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[2-(^2H₁₁)cyclohexyl-4-methyl-6-oxopyridin-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[(6-Cyclohexyl-d11-4-methyl-2-oxo-1(2H)-pyridinyl)oxy]-1-deoxy-β-D-glucopyranuronic Acid; Ciclopirox-d11 β-D-Glucuronide

Database IDs

• PubChem SID: 162258887
• PubChem CID: 71314864

CALCULATED PROPERTIES

• Acid pKa: 3.347076
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.6372288
• LogD (pH = 7.4): -2.9148405
• Log P: 0.5008626
• Molar Refractivity: 92.9192 cm^3
• Polarizability: 36.38655 Å^3
• Polar Surface Area: 136.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C432812

A labelled metabolite of Ciclopirox.

REFERENCES

• Kellner, H.M., et al.: Arzneim.-Forch., 31, 1337 (1981)