prop-2-en-1-yl (2S,3S,4S,5R,6S)-6-{4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoyloxy}-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 169524
• Molecular Formular: C21H23ClN2O11S
• Molecular Mass: 546.93212
• Monoisotopic Mass: 546.07110825
• SMILES: c1ccc(o1)CNc1cc(c(cc1C(=O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)OCC=C)O)O)O)S(=O)(=O)N)Cl
• Canonical SMILES: C=CCOC(=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/C21H23ClN2O11S/c1-2-5-33-20(29)18-16(26)15(25)17(27)21(34-18)35-19(28)11-7-14(36(23,30)31)12(22)8-13(11)24-9-10-4-3-6-32-10/h2-4,6-8,15-18,21,24-27H,1,5,9H2,(H2,23,30,31)/t15-,16-,17+,18-,21-/m0/s1
• InChIKey: AIEKHEVMCOBIBQ-CURYNPBISA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162263656
• PubChem CID: 71317018

CALCULATED PROPERTIES

• Acid pKa: 9.510429
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 0.8777148
• LogD (pH = 7.4): 0.8747803
• Log P: 0.87775236
• Molar Refractivity: 123.7046 cm^3
• Polarizability: 48.882202 Å^3
• Polar Surface Area: 207.85 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - F865020

Intermediate for the synthesis of Furosemide Acyl-β-D-glucuronide.