(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-5-methyl-2,3-dihydrofuran-3-one

• ChemBase ID: 171655
• Molecular Formular: C12H10O4
• Molecular Mass: 218.2054
• Monoisotopic Mass: 218.0579088
• SMILES: c1(cc(c(cc1)O)O)/C=C\1/OC(=CC1=O)C
• Canonical SMILES: CC1=CC(=O)/C(=C\c2ccc(c(c2)O)O)/O1
• InChI: InChI=1S/C12H10O4/c1-7-4-11(15)12(16-7)6-8-2-3-9(13)10(14)5-8/h2-6,13-14H,1H3/b12-6+
• InChIKey: NLZQGBCUKNUDED-WUXMJOGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-[(3,4-dihydroxyphenyl)methylidene]-5-methyl-2,3-dihydrofuran-3-one
• IUPAC Traditional name: (2E)-2-[(3,4-dihydroxyphenyl)methylidene]-5-methylfuran-3-one
• Synonyms: (2E)-2-[(3,4-Dihydroxyphenyl)methylene]-5-methyl-3(2H)-furanone; Inotilone

Database IDs

• CAS Number: 906366-79-8
• PubChem SID: 164227565
• PubChem CID: 29982319

CALCULATED PROPERTIES

• Acid pKa: 8.830937
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.6790475
• LogD (pH = 7.4): 1.6635474
• Log P: 1.6792487
• Molar Refractivity: 61.4746 cm^3
• Polarizability: 22.225933 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I666500

A potent COX-2 inhibitor. Inotilone is used for treating degenerative conditions from overexpression of iNOS.

REFERENCES

• McGeer, E., et al.: Biodrugs, 19, 31 (2005)
• Samoha, S., et al.: Oncology, 69, 33 (2005)
• Sinicrope, F., et al.: Mol. Carcinogen, 45, 447 (2005)
• Uray, I., et al.: Expert. Opin. Inv. Drug, 15, 1583 (2005)