CAS 486-35-1|7,8-Dihydroxychromen-2-one|daphnetin|7,8-dihydroxy-2H-chromen-2-one|Daphnetin |Daphnetin|Daphnetol|Daphnetin|7,8-dihydroxy-2H-chromen-2-one|7,8-Dihydroxycoumarin

General Information

Structure

Molecular Formula

C₉H₆O₄

Molecular Mass

178.14154

Exact Mass

178.02660867

Charge

InChI

InChI=1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H

InChIKey

ATEFPOUAMCWAQS-UHFFFAOYSA-N

Canonic Smiles

O=c1ccc2c(o1)c(O)c(cc2)O

Isomeric Smiles

c12oc(=O)ccc1ccc(O)c2O

Calculated Properties

JChem

Acid pKa

8.045391

H Acceptors

H Donor

LogD (pH = 5.5)

1.8250022

LogD (pH = 7.4)

1.7383214

Log P

1.826229

Molar Refractivity

45.5104

Polarizability

16.96474

Polar Surface Area

66.76

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

7,8-Dihydroxychromen-2-oneDaphnetin DaphnetinDaphnetolDaphnetin7,8-Dihydroxycoumarin

IUPAC Traditional name

daphnetin 7,8-dihydroxy-2H-chromen-2-one

IUPAC name

7,8-dihydroxy-2H-chromen-2-one

Names and Identifiers

Registration numbers

CAS Number

486-35-1

PubChem SID

2488234224278375162029303

EC Number

207-632-8

MDL Number

MFCD00016977

PubChem CID

5280569

Registration numbers

Properties

Physical Property

Apperance

solid

Pharmacology Properties

Mechanism of Action

Antioxydant

Inhibitor of various protein kinases

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S2554

Research Area: Cancer
Biological Activity:
It is also a chelator and an antioxidant. In vitro, daphnetin causes a 50% inhibition (IC50) of 3H-hypoxanthine incorporation by Plasmodium falciparum at concentrations between 25 and 40 µM.

Sigma Aldrich

630764

Packaging
5 g in glass bottle

D5564

Biochem/physiol Actions
Inhibitor of protein kinases.
Packaging
5, 25 mg in glass bottle

Molecule Details

References

PubChem Literature

From Data Sources

• Mendz, J. et al., Microchem. J., 1969, 14, 567, (uv)

• Sato, M. et al., Phytochemistry, 1972, 11, 657; 2367, (biosynth)

• Gnther, H. et al., Org. Magn. Reson., 1975, 7, 339, (cmr, deriv)

• Joseph-Nathan, P. et al., J. Het. Chem., 1984, 21, 1141, (pmr, deriv)

• Wildenhaim, W. et al., J. Prakt. Chem., 1970, 312, 690, (isol)

• Pastor, R.E. et al., Can. J. Chem., 1987, 65, 1356, (cmr)

• Bohm, B.A. et al., Can. J. Biochem., 1961, 39, 1389, (struct)

• Cussans, N.J. et al., Tetrahedron, 1975, 31, 2719, (cmr)

• Jurd, L. et al., Aust. J. Chem., 1974, 27, 2697, (synth)

• Abyshev, A.Z., Khim. Prir. Soedin., 1974, 10, 568; Chem. Nat. Compd. (Engl. Transl.), 1974, 10, 581, (isol)

• Brown, S.A. et al., Phytochemistry, 1964, 469, (biosynth)

• Rybalko, K.S. et al., Khim. Prir. Soedin., 1976, 12, 294; Chem. Nat. Compd. (Engl. Transl.), 1976, 12, 262, (isol)

• Gray, A.I. et al., Phytochemistry, 1981, 26, 1171; 1987, 257, (derivs)

• Shimomura, H. et al., Chem. Pharm. Bull., 1980, 347, (deriv)

• MacLeod, J.K. et al., Aust. J. Chem., 1978, 31, 1545, (synth)

• Borges del Castillo, J. et al., Phytochemistry, 1984, 23, 859, (derivs)

• Barnes, C.S. et al., Aust. J. Chem., 1964, 17, 975, (ms)

• Herz, W. et al., Phytochemistry, 1970, 9, 891, (isol)

• Reisch, J. et al., Monatsh. Chem., 1988, 119, 1333, (synth)

• Jain, B.D., Anal. Chim. Acta, 1967, 37, 1358, (use)

• Barua, N.C. et al., Phytochemistry, 1980, 19, 2217, (deriv)

• Ueno, K. et al., Acta Cryst. B, 1976, 31, 946, (cryst struct)

• Brown, S.A., Z. Naturforsch., C, 1986, 41, 247, (biosynth)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

7,8-Dihydroxychromen-2-oneDaphnetin DaphnetinDaphnetolDaphnetin7,8-Dihydroxycoumarin

IUPAC Traditional name

daphnetin 7,8-dihydroxy-2H-chromen-2-one

IUPAC name

7,8-dihydroxy-2H-chromen-2-one

Registration numbers

CAS Number

486-35-1

PubChem SID

2488234224278375162029303

EC Number

MDL Number

PubChem CID

Molecule Details

S2554

630764

Packaging
5 g in glass bottle

D5564

Biochem/physiol Actions
Inhibitor of protein kinases.
Packaging
5, 25 mg in glass bottle

References

PubChem Literature

From Data Sources

• Mendz, J. et al., Microchem. J., 1969, 14, 567, (uv)

• Sato, M. et al., Phytochemistry, 1972, 11, 657; 2367, (biosynth)

• Gnther, H. et al., Org. Magn. Reson., 1975, 7, 339, (cmr, deriv)

• Joseph-Nathan, P. et al., J. Het. Chem., 1984, 21, 1141, (pmr, deriv)

• Wildenhaim, W. et al., J. Prakt. Chem., 1970, 312, 690, (isol)

• Pastor, R.E. et al., Can. J. Chem., 1987, 65, 1356, (cmr)

• Bohm, B.A. et al., Can. J. Biochem., 1961, 39, 1389, (struct)

• Cussans, N.J. et al., Tetrahedron, 1975, 31, 2719, (cmr)

• Jurd, L. et al., Aust. J. Chem., 1974, 27, 2697, (synth)

• Abyshev, A.Z., Khim. Prir. Soedin., 1974, 10, 568; Chem. Nat. Compd. (Engl. Transl.), 1974, 10, 581, (isol)

• Brown, S.A. et al., Phytochemistry, 1964, 469, (biosynth)

• Rybalko, K.S. et al., Khim. Prir. Soedin., 1976, 12, 294; Chem. Nat. Compd. (Engl. Transl.), 1976, 12, 262, (isol)

• Gray, A.I. et al., Phytochemistry, 1981, 26, 1171; 1987, 257, (derivs)

• Shimomura, H. et al., Chem. Pharm. Bull., 1980, 347, (deriv)

• MacLeod, J.K. et al., Aust. J. Chem., 1978, 31, 1545, (synth)

• Borges del Castillo, J. et al., Phytochemistry, 1984, 23, 859, (derivs)

• Barnes, C.S. et al., Aust. J. Chem., 1964, 17, 975, (ms)

• Herz, W. et al., Phytochemistry, 1970, 9, 891, (isol)

• Reisch, J. et al., Monatsh. Chem., 1988, 119, 1333, (synth)

• Jain, B.D., Anal. Chim. Acta, 1967, 37, 1358, (use)

• Barua, N.C. et al., Phytochemistry, 1980, 19, 2217, (deriv)

• Ueno, K. et al., Acta Cryst. B, 1976, 31, 946, (cryst struct)

• Brown, S.A., Z. Naturforsch., C, 1986, 41, 247, (biosynth)

Bioactivity

PubChem BioAssay

Properties

Physical Property

Apperance

solid

Pharmacology Properties

Mechanism of Action

Antioxydant

Inhibitor of various protein kinases

Molecule

ID:63564