(2S,3S,4S,5R,6S)-6-({[1-(1-benzothiophen-2-yl)ethyl](carbamoyl)amino}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 179578
• Molecular Formular: C17H20N2O8S
• Molecular Mass: 412.4143
• Monoisotopic Mass: 412.09403661
• SMILES: c1cccc2c1sc(c2)C(C)N(C(=O)N)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](ON(C(c2cc3c(s2)cccc3)C)C(=O)N)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C17H20N2O8S/c1-7(10-6-8-4-2-3-5-9(8)28-10)19(17(18)25)27-16-13(22)11(20)12(21)14(26-16)15(23)24/h2-7,11-14,16,20-22H,1H3,(H2,18,25)(H,23,24)/t7?,11-,12-,13+,14-,16-/m0/s1
• InChIKey: CYYKQHWQVGZJRJ-UPZRFPAJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({[1-(1-benzothiophen-2-yl)ethyl](carbamoyl)amino}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({[1-(1-benzothiophen-2-yl)ethyl](carbamoyl)amino}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-O-[(Aminocarbonyl)(1-benzo[b]thien-2-ylethyl)amino]-β-D-glucopyranuronic Acid; Zileuton β-D-Glucuronide

Database IDs

• CAS Number: 141056-63-5
• PubChem SID: 164235488
• PubChem CID: 71752997

CALCULATED PROPERTIES

• Acid pKa: 4.0297813
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.1904651
• LogD (pH = 7.4): -2.8512988
• Log P: 0.29044595
• Molar Refractivity: 93.9713 cm^3
• Polarizability: 38.64756 Å^3
• Polar Surface Area: 162.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - Z420010

A metabolite of Zileuton (Z420000).

REFERENCES

• Sweeny, D.J., et al.: Metab. Dispos., 20, 328 (1992)