CAS 518-82-1|CAS 60529-33-1|6-methyl-1,3,8-trihydroxyanthraquinone|Emodin|3-METHYL-1,6,8-TRIHYDROXYANTHRAQUINONE|1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione|emodin|1,3,8-Trihydroxy-6...

General Information

Structure

Molecular Formula

C₁₅H₁₀O₅

Molecular Mass

270.2369

Exact Mass

270.05282342

Charge

InChI

InChI=1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3

InChIKey

RHMXXJGYXNZAPX-UHFFFAOYSA-N

Canonic Smiles

Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)O

Isomeric Smiles

c1(O)cc(O)cc2C(=O)c3cc(C)cc(O)c3C(=O)c12

Calculated Properties

JChem

LogD (pH = 7.4)

3.43

LogD (pH = 5.5)

3.81

Log P

3.82

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

7.29

Polar Surface Area

94.83

Polarizability

26.57

Molar Refractivity

72.13

LOG S

-3.70

Data Source

Names and Identifiers

Synonyms

6-methyl-1,3,8-trihydroxyanthraquinoneEmodin3-METHYL-1,6,8-TRIHYDROXYANTHRAQUINONE1,3,8-Trihydroxy-6-methylanthraquinoneFrangula-emodinEmodol6-Methyl-1,3,8-tri-hydroxy-anthra-quinone1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione1,3,8-Tri-hydroxy-6-methyl-anthra-quinoneEmodinArchinRheum-emodinFrangula emodinAlatinoneFrangulinic acidSchuttgelbemodin1,3,8-trihydroxy-6-methyl-9,10-anthraquinone1,3,8-trihydroxy-6-methyl-9,10-anthracenedioneEmodin3-METHYL-1,6,8-TRIHYDROXYANTHRAQUINONE

IUPAC name

1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione

IUPAC Traditional name

emodin 1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione

Names and Identifiers

Registration numbers

Properties

Pharmacology Properties

human ... CSNK2A1(1457), CSNK2B(1460), ELA2(1991), NFKB1(4790), NKAP(79576), NKRF(55922)

human ... ELA2(1991)

Monoamine oxidase inhibitor

Inhibitor of phosphoinositide- 3-kinase (PI3K)/AKT

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S2295

Research Area: Inflammation
Biological Activity:
Emodin is a purgative resin, 6-methyl-1,3,8-trihydroxyanthraquinone, from rhubarb, the buckthorn and Japanese Knotweed (Fallopia japonica). It belongs to a family of compounds called anthraquinones, which have shown anti-inflammatory and anticancer effects. [1][2]

MP Biomedicals

02190453

From Frangula Bark
Purity: ~98%
A protein tyrosine kinase inhibitor.

02199021

Purity:>95% (HPLC)

05206347

MP Biomedicals Rare Chemical collection

Wikipedia

Emodin

Sigma Aldrich

E7881

Biochem/physiol Actions
Inhibitor of NF-κB activation and adhesion molecule expression. Casein Kinase 2 (CK2) inhibitor.
Packaging
50, 250 mg in poly bottle

DrugBank

DB07715

Drug information: experimental

ChEBI

CHEBI:42223

A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs.

Molecule Details

References

PubChem Literature

From Data Sources

• http://www.cancer.gov/dictionary/?CdrID=330167

• Banville, J. et al., J.C.S. Perkin 1, 1976, 1852

• Kalidhar, S.B., Phytochemistry, 1989, 28, 2455; 3459, (pmr)

• Steglich, W. et al., Chem. Ber., 1972, 105, 2928

• Wagner, H., Tet. Lett., 1972, 5013

• Macias, M. et al., J. Nat. Prod., 2000, 63, 757-761, (Emodin, activity)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 88D, (ir)

• Hrhammer, H.P. et al., Z. Naturforsch., B, 1972, 27, 959

• Okabe, H., Chem. Pharm. Bull., 1973, 21, 1254

• Fairbairn, J.W., Pharmacology, Suppl. 1, 1976, 14, 1, (rev)

• Fujimoto, H. et al., Chem. Pharm. Bull., 1998, 46, 1506-1510, (isol, activity)

• Schmidt, R.R. et al., Synthesis, 1994, 255, (synth, pmr)

• Francis, G.W. et al., Magn. Reson. Chem., 1998, 36, 769-772, (pmr, cmr, Frangulins, Glucofrangulins)

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 91D, (nmr)

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 1265; 1274, (occur)

• Eder, R. et al., Helv. Chim. Acta, 1925, 8, 140, (bibl)

• Hirose, Y. et al., Chem. Pharm. Bull., 1973, 21, 2790, (synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MQF250

• Kelly, T.R. et al., J.O.C., 1983, 48, 3573, (isol)

• Sigma-Aldrich Library of Stains, Dyes and Indicators, 298

• Banville, J. et al., Can. J. Chem., 1974, 52, 80, (synth, uv, ir, pmr)

• Anderson, J.A. et al., Phytochemistry, 1986, 25, 1115, (biosynth)

• Wang, E.-C. et al., Heterocycles, 1996, 43, 969, (isol, uv, ir, pmr, cmr, ms)

• Ahmed, S.A. et al., Chem. Comm., 1987, 883, (synth)

• Hassall, C.H. et al., J.C.S. Perkin 1, 1973, 2853, (synth, derivs)

• Coskun, M. et al., Phytochemistry, 1990, 29, 2018, (cd, pmr, cmr)

• Cole, R.J. et al., Handbook of Toxic Fungal Metabolites, Academic Press, New York, 1981, 684

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione

IUPAC Traditional name

emodin 1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione

Molecule Details

Selleck Chemicals

S2295

MP Biomedicals

02190453

From Frangula Bark
Purity: ~98%
A protein tyrosine kinase inhibitor.

02199021

Purity:>95% (HPLC)

05206347

MP Biomedicals Rare Chemical collection

Wikipedia

Emodin

Sigma Aldrich

E7881

Biochem/physiol Actions
Inhibitor of NF-κB activation and adhesion molecule expression. Casein Kinase 2 (CK2) inhibitor.
Packaging
50, 250 mg in poly bottle

DrugBank

DB07715

Drug information: experimental

ChEBI

CHEBI:42223

References

PubChem Literature

From Data Sources

• http://www.cancer.gov/dictionary/?CdrID=330167

• Banville, J. et al., J.C.S. Perkin 1, 1976, 1852

• Kalidhar, S.B., Phytochemistry, 1989, 28, 2455; 3459, (pmr)

• Steglich, W. et al., Chem. Ber., 1972, 105, 2928

• Wagner, H., Tet. Lett., 1972, 5013

• Macias, M. et al., J. Nat. Prod., 2000, 63, 757-761, (Emodin, activity)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 88D, (ir)

• Hrhammer, H.P. et al., Z. Naturforsch., B, 1972, 27, 959

• Okabe, H., Chem. Pharm. Bull., 1973, 21, 1254

• Fairbairn, J.W., Pharmacology, Suppl. 1, 1976, 14, 1, (rev)

• Fujimoto, H. et al., Chem. Pharm. Bull., 1998, 46, 1506-1510, (isol, activity)

• Schmidt, R.R. et al., Synthesis, 1994, 255, (synth, pmr)

• Francis, G.W. et al., Magn. Reson. Chem., 1998, 36, 769-772, (pmr, cmr, Frangulins, Glucofrangulins)

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 91D, (nmr)

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 1265; 1274, (occur)

• Eder, R. et al., Helv. Chim. Acta, 1925, 8, 140, (bibl)

• Hirose, Y. et al., Chem. Pharm. Bull., 1973, 21, 2790, (synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MQF250

• Kelly, T.R. et al., J.O.C., 1983, 48, 3573, (isol)

• Sigma-Aldrich Library of Stains, Dyes and Indicators, 298

• Banville, J. et al., Can. J. Chem., 1974, 52, 80, (synth, uv, ir, pmr)

• Anderson, J.A. et al., Phytochemistry, 1986, 25, 1115, (biosynth)

• Wang, E.-C. et al., Heterocycles, 1996, 43, 969, (isol, uv, ir, pmr, cmr, ms)

• Ahmed, S.A. et al., Chem. Comm., 1987, 883, (synth)

• Hassall, C.H. et al., J.C.S. Perkin 1, 1973, 2853, (synth, derivs)

• Coskun, M. et al., Phytochemistry, 1990, 29, 2018, (cd, pmr, cmr)

• Cole, R.J. et al., Handbook of Toxic Fungal Metabolites, Academic Press, New York, 1981, 684

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

human ... CSNK2A1(1457), CSNK2B(1460), ELA2(1991), NFKB1(4790), NKAP(79576), NKRF(55922)

human ... ELA2(1991)

Monoamine oxidase inhibitor

Inhibitor of phosphoinositide- 3-kinase (PI3K)/AKT

Molecule

ID:5353