(2S,3S,4S,5R,6S)-6-{4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 169523
• Molecular Formular: C18H19ClN2O11S
• Molecular Mass: 506.86826
• Monoisotopic Mass: 506.03980812
• SMILES: c1(CNc2cc(c(cc2C(=O)O[C@H]2[C@H]([C@H]([C@@H]([C@@H](O2)C(=O)O)O)O)O)S(=O)(=O)N)Cl)occc1
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(=O)c2cc(c(cc2NCc2ccco2)Cl)S(=O)(=O)N)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C18H19ClN2O11S/c19-9-5-10(21-6-7-2-1-3-30-7)8(4-11(9)33(20,28)29)17(27)32-18-14(24)12(22)13(23)15(31-18)16(25)26/h1-5,12-15,18,21-24H,6H2,(H,25,26)(H2,20,28,29)/t12-,13-,14+,15-,18-/m0/s1
• InChIKey: RNVHHPUYELVHRE-GLRLOKQVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoate] -β-D-glucopyranuronic Acid; Furosemide Glucuronide; Furosemide Acyl-β-D-glucuronide

Database IDs

• CAS Number: 72967-59-0
• PubChem SID: 162263655
• PubChem CID: 21123459

CALCULATED PROPERTIES

• Acid pKa: 2.5609312
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -2.8397303
• LogD (pH = 7.4): -3.5110517
• Log P: 6.0850335E-4
• Molar Refractivity: 109.7728 cm^3
• Polarizability: 43.48002 Å^3
• Polar Surface Area: 218.85 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Hot Water
• Apperance: Yellow Solid
• Melting Point: 143-146°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - F865010

A metabolite of Furosemide (F865000).