3-[(E)-[(2-hydroxyphenyl)methylidene]amino]-2H-chromen-2-one

• ChemBase ID: 177681
• Molecular Formular: C16H11NO3
• Molecular Mass: 265.26344
• Monoisotopic Mass: 265.07389322
• SMILES: c1cccc2c1cc(c(=O)o2)/N=C/c1ccccc1O
• Canonical SMILES: Oc1ccccc1/C=N/c1cc2ccccc2oc1=O
• InChI: InChI=1S/C16H11NO3/c18-14-7-3-1-6-12(14)10-17-13-9-11-5-2-4-8-15(11)20-16(13)19/h1-10,18H/b17-10+
• InChIKey: UCXAFCDYVZFKKR-LICLKQGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(E)-[(2-hydroxyphenyl)methylidene]amino]-2H-chromen-2-one
• IUPAC Traditional name: 3-[(E)-[(2-hydroxyphenyl)methylidene]amino]chromen-2-one
• Synonyms: 3-[(E)-[(2-Hydroxyphenyl)methylene]amino]-2H-1-benzopyran-2-one; 3-(Salicylideneamino) Coumarin

Database IDs

• CAS Number: 910217-51-5
• PubChem SID: 164233591
• PubChem CID: 6101838

CALCULATED PROPERTIES

• Acid pKa: 8.822134
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.1430852
• LogD (pH = 7.4): 3.1273122
• Log P: 3.1433337
• Molar Refractivity: 76.8314 cm^3
• Polarizability: 28.452173 Å^3
• Polar Surface Area: 58.89 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetic Acid; DMF
• Apperance: Orange Cyrstalline Solid
• Melting Point: 197-198°C

Safety Information

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

DETAILS

Toronto Research Chemicals - S088500

A coumarin derivative which shows antiinflammatory activity against carrageenan-induced edema.

REFERENCES

• Maddi, V., et al.: J. Pharm. Sci., 81, 964 (1992)