(2S,3S,4S,5R,6S)-6-[3-(butylamino)-4-phenoxy-5-sulfamoylbenzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 163103
• Molecular Formular: C23H28N2O11S
• Molecular Mass: 540.54022
• Monoisotopic Mass: 540.14138073
• SMILES: c1(cc(c(c(c1)S(=O)(=O)N)Oc1ccccc1)NCCCC)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CCCCNc1cc(cc(c1Oc1ccccc1)S(=O)(=O)N)C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H28N2O11S/c1-2-3-9-25-14-10-12(11-15(37(24,32)33)19(14)34-13-7-5-4-6-8-13)22(31)36-23-18(28)16(26)17(27)20(35-23)21(29)30/h4-8,10-11,16-18,20,23,25-28H,2-3,9H2,1H3,(H,29,30)(H2,24,32,33)/t16-,17-,18+,20-,23-/m0/s1
• InChIKey: MXEVQINQQGRZRQ-RZUKHUMYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[3-(butylamino)-4-phenoxy-5-sulfamoylbenzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[3-(butylamino)-4-phenoxy-5-sulfamoylbenzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[3-(Aminosulfonyl)-5-(butylamino)-4-phenoxybenzoate]-β-D-glucopyranuronic Acid; Bumetanide Glucuronide; Bumetanide β-D-Glucuronide

Database IDs

• CAS Number: 102623-14-3
• PubChem SID: 162257238
• PubChem CID: 71314302

CALCULATED PROPERTIES

• Acid pKa: 1.8081998
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -2.0988731
• LogD (pH = 7.4): -2.7301953
• Log P: 0.16301988
• Molar Refractivity: 128.0789 cm^3
• Polarizability: 50.687973 Å^3
• Polar Surface Area: 214.94 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B689605

A metabolite of Bumetanide (B689550).

REFERENCES

• Van Breemen, R.B., et al.: Drug Metab. Dispos., 14, 197 (1986)
• Han, K.S., et al.: Biopharma. Drug Dispos., 14, 533 (1986)