5-{2-fluoro-5-[(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]prop-1-en-1-yl]phenyl}-1,2-oxazole-3-carboxylic acid

• ChemBase ID: 1780
• Molecular Formular: C21H16FNO7
• Molecular Mass: 413.3526432
• Monoisotopic Mass: 413.09108008
• SMILES: c1(c(cc(cc1)/C=C/COc1cccc(c1C(=O)OC)O)c1onc(c1)C(=O)O)F
• Canonical SMILES: COC(=O)c1c(OC/C=C/c2ccc(c(c2)c2onc(c2)C(=O)O)F)cccc1O
• InChI: InChI=1S/C21H16FNO7/c1-28-21(27)19-16(24)5-2-6-17(19)29-9-3-4-12-7-8-14(22)13(10-12)18-11-15(20(25)26)23-30-18/h2-8,10-11,24H,9H2,1H3,(H,25,26)/b4-3+
• InChIKey: QKHWJUMLYAYZFS-ONEGZZNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{2-fluoro-5-[(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]prop-1-en-1-yl]phenyl}-1,2-oxazole-3-carboxylic acid
• IUPAC Traditional name: @compound 9
• Synonyms: 5-{2-fluoro-5-[3-(3-hydroxy-2-methoxycarbonyl-phenoxy)-propenyl]-phenyl}-isoxazole-3-carboxylic acid; Compound 9

Database IDs

• PubChem SID: 160965236; 46506116
• PubChem CID: 447994

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.903953
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.0158746
• LogD (pH = 7.4): 1.4044528
• Log P: 4.617782
• Molar Refractivity: 105.0149 cm^3
• Polarizability: 40.01865 Å^3
• Polar Surface Area: 119.09 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.29
• LOG S: -4.09
• Solubility (Water): 3.37e-02 g/l

DETAILS

DrugBank - DB02014

Drug information: experimental