8-(2-hydroxypropan-2-yl)-2H,8H,9H-furo[2,3-h]chromen-2-one

• ChemBase ID: 164947
• Molecular Formular: C14H14O4
• Molecular Mass: 246.25856
• Monoisotopic Mass: 246.08920893
• SMILES: o1c2c(ccc1=O)ccc1c2CC(O1)C(O)(C)C
• Canonical SMILES: O=c1ccc2c(o1)c1CC(Oc1cc2)C(O)(C)C
• InChI: InChI=1S/C14H14O4/c1-14(2,16)11-7-9-10(17-11)5-3-8-4-6-12(15)18-13(8)9/h3-6,11,16H,7H2,1-2H3
• InChIKey: YRAQEMCYCSSHJG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-(2-hydroxypropan-2-yl)-2H,8H,9H-furo[2,3-h]chromen-2-one
• IUPAC Traditional name: (+-)-columbianetin
• Synonyms: (8S)-8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]-1-benzopyran-2-one; (S)-8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]-1-benzopyran-2-one; Columbianetin; (+)-Columbianetin

Database IDs

• CAS Number: 3804-70-4
• PubChem SID: 162259081
• PubChem CID: 150888

CALCULATED PROPERTIES

• Acid pKa: 14.29667
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.7323936
• LogD (pH = 7.4): 1.7323935
• Log P: 1.7323936
• Molar Refractivity: 66.3409 cm^3
• Polarizability: 25.41187 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C642500

Columbianetin inhibited expression of COX-2. It may be helpful in regulating mast cell-mediated allergic inflammatory responses. An anti-inflammatory agent.

REFERENCES

• Ng, T., et al.: Life Sci., 66, 709 (2000)
• Gurish, M., et al.: J. Exp. Med., 194, F1 (2000)
• Hougee, S., et al.: Biochem. Pharmacol., 69, 241 (2000)
• Kang, S., et al.: Arch. Pharm. Res., 30, 1368 (2000)