CAS 484-20-8|4-methoxy-7H-furo[3,2-g]chromen-7-one|5-METHOXYPSORALEN|bergapten|Bergapten|5-Methoxypsoralen|4-甲氧基-7H-呋喃并[3,2-g]苯并吡喃-7-酮|Bergapten|4-Methoxyfuro[3,2-g]benzopyrane-7-one|佛手...

General Information

Structure

Molecular Formula

C₁₂H₈O₄

Molecular Mass

216.18952

Exact Mass

216.04225874

Charge

InChI

InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3

InChIKey

BGEBZHIAGXMEMV-UHFFFAOYSA-N

Canonic Smiles

COc1c2ccc(=O)oc2cc2c1cco2

Isomeric Smiles

COc1c2ccc(=O)oc2cc2c1cco2

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

1.7848117

LogD (pH = 7.4)

1.7848117

Log P

1.7848117

Molar Refractivity

56.8529

Polarizability

22.595345

Polar Surface Area

48.67

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

4-methoxy-7H-furo[3,2-g]chromen-7-one

Synonyms

5-METHOXYPSORALENBergapten5-Methoxypsoralen4-甲氧基-7H-呋喃并[3,2-g]苯并吡喃-7-酮Bergapten4-Methoxyfuro[3,2-g]benzopyrane-7-one佛手柑内酯5-甲氧基补骨脂素Bergapten5-Methoxypsoralen4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-oneBergaptene5-MOP, Psoraderm-5HeraclinBergaptanMajudin4-Methoxy-7H-furo[3,2-g]chromen-7-one

IUPAC Traditional name

bergapten 4-methoxy-7H-furo[3,2-g]chromen-7-one

Names and Identifiers

Registration numbers

CAS Number

EC Number

KEGG ID

Wikipedia Title

ATC CODE

CHEMBL

Unique Ingredient Identifier

PubChem CID

Chemspider ID

Beilstein Number

MDL Number

PubChem SID

2485666716209303724883936

Registration numbers

Properties

Pharmacology Properties

Oral

Radiosensitizer

Spasmolytic

Others

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Wikipedia

Bergapten

Sigma Aldrich

275727

Packaging
1 g in glass bottle
250 mg in glass bottle

65320

Other Notes
Intercalating agent for DNA forming covalent cross-links upon UV-irradiation1,2,3

TRC

B318500

Naturally occurring analog of Psoralen ( P839800) and metabolite of 8-Methoxy Psoralen (M260795). Antipsoriatic.

Molecule Details

References

PubChem Literature

From Data Sources

• Honigsmann, H., et al.: Br. J. Dermatol., 101, 369 (1979)

• Austin, D.J. et al., Phytochemistry, 1973, 12, 1657, (biosynth)

• Baetcke, E. et al., Ber., 1912, 45, 3705, (struct)

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 1369, (occur, deriv)

• Masuda, T. et al., Phytochemistry, 1998, 47, 13-16, (Bergapten, isol, pmr, cmr)

• Boyd, R.K. et al., Can. J. Chem., 1979, 57, 1995, (ms)

• Diawara, M.M. et al., J. Agric. Food Chem., 1995, 43, 723-727, (occur)

• Kubiczek, G. et al., Ber., 1937, 70, 1253, (synth)

• Gu, Z. et al., Chem. Pharm. Bull., 1990, 38, 2498, (deriv)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1321A, (nmr)

• IARC Monog., 1986, 40, 327, (tox, rev)

• Ginderow, D., Acta Cryst. C, 1991, 47, 2144, (cryst struct)

• Glatfelder, A. et al., Helv. Chim. Acta, 1920, 3, 541; 1921, 4, 718, (synth)

• Kawaii, S. et al., J. Agric. Food Chem., 1999, 47, 4073, (activity)

• Oliva, A. et al., J. Chem. Ecol., 1999, 25, 519-526, (activity)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MFN275

• Socias, L. et al., Ber., 1934, 67, 59, (isol)

• Duddeck, H. et al., Phytochemistry, 1979, 18, 139, (cmr)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

4-methoxy-7H-furo[3,2-g]chromen-7-one

Synonyms

IUPAC Traditional name

bergapten 4-methoxy-7H-furo[3,2-g]chromen-7-one

Registration numbers

CAS Number

EC Number

KEGG ID

Wikipedia Title

ATC CODE

CHEMBL

Unique Ingredient Identifier

PubChem CID

Chemspider ID

Beilstein Number

MDL Number

PubChem SID

2485666716209303724883936

Molecule Details

Wikipedia

Bergapten

Sigma Aldrich

275727

Packaging
1 g in glass bottle
250 mg in glass bottle

65320

Other Notes
Intercalating agent for DNA forming covalent cross-links upon UV-irradiation1,2,3

TRC

B318500

Naturally occurring analog of Psoralen ( P839800) and metabolite of 8-Methoxy Psoralen (M260795). Antipsoriatic.

References

PubChem Literature

From Data Sources

• Honigsmann, H., et al.: Br. J. Dermatol., 101, 369 (1979)

• Austin, D.J. et al., Phytochemistry, 1973, 12, 1657, (biosynth)

• Baetcke, E. et al., Ber., 1912, 45, 3705, (struct)

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 1369, (occur, deriv)

• Masuda, T. et al., Phytochemistry, 1998, 47, 13-16, (Bergapten, isol, pmr, cmr)

• Boyd, R.K. et al., Can. J. Chem., 1979, 57, 1995, (ms)

• Diawara, M.M. et al., J. Agric. Food Chem., 1995, 43, 723-727, (occur)

• Kubiczek, G. et al., Ber., 1937, 70, 1253, (synth)

• Gu, Z. et al., Chem. Pharm. Bull., 1990, 38, 2498, (deriv)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1321A, (nmr)

• IARC Monog., 1986, 40, 327, (tox, rev)

• Ginderow, D., Acta Cryst. C, 1991, 47, 2144, (cryst struct)

• Glatfelder, A. et al., Helv. Chim. Acta, 1920, 3, 541; 1921, 4, 718, (synth)

• Kawaii, S. et al., J. Agric. Food Chem., 1999, 47, 4073, (activity)

• Oliva, A. et al., J. Chem. Ecol., 1999, 25, 519-526, (activity)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MFN275

• Socias, L. et al., Ber., 1934, 67, 59, (isol)

• Duddeck, H. et al., Phytochemistry, 1979, 18, 139, (cmr)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Oral

Radiosensitizer

Spasmolytic

Others

Molecule

ID:104315