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Structure Database (LMSD)

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Common Name

Emodin

Systematic Name

1,3,8-trihydroxy-6-methylanthracene-9,10-dione

Synonyms

LM ID

LMPK13040008

Formula

C₁₅H₁₀O₅

Exact Mass

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270.052825

Status

Curated

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Classification

Category

Main Class

Sub Class

Polyketides [PK]

Aromatic polyketides [PK13]

Anthracenes and phenanthrenes [PK1304]

Biological Context

Emodin is a naturally-occurring anthraquinone found in a variety of plants used in traditional Chinese medicine. Purified emodin has diverse effects, including the suppression of inflammation, dyslipidemia, and cancer.^1,2,3 At a molecular level, emodin directly and selectively inhibits casein kinase II (IC50 = 0.89 μM).^4,5 Through this action, it inhibits the COP9 signalosome, causing the stabilization of the tumor suppressor p53.5 Moreover, emodin acts as a phytoestrogen, binding human estrogen receptors and blocking 17β-estradiol binding with Ki values of 0.77 and 1.5 μM for ERα and ERβ, respectively.⁶

This information has been provided by Cayman Chemical

References

1. Alisi, A., Pastore, A., Ceccarelli, S., et al. Emodin prevents intrahepatic fat accumulation, inflammation and redox status imbalance during diet-induced hepatosteatosis in rats. Int. J. Mol. Sci. 13(2), 2276-2289 (2012).

2. Lin, S.Z., Wei, W.T., Chen, H., et al. Antitumor activity of emodin against pancreatic cancer depends on its dual role: Promotion of apoptosis and suppression of angiogenesis. PLoS One 7(8), 1-15 (2012).

3. Tzeng, T.F., Lu, H.J., Liou, S.S., et al. Emodin, a naturally occurring anthraquinone derivative, ameliorates dyslipidemia by activating AMP-activated protein kinase in high-fat-diet-fed rats. Evid. Based Complement. Alternat. Med. 781812 (2012).

4. Füllbeck, M., Huang, X., Dumdey, R., et al. Novel curcumin- and emodin-related compounds identified by in silico 2D/3D conformer screening induce apoptosis in tumor cells. BMC Cancer 5(97), 1-14 (2005).

5. Matsuda, H., Shimoda, H., Morikawa, T., et al. Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): Structure-requirement of hydroxyanthraquinones for estrogenic activity. Bioorg. Med. Chem. Lett. 11(14), 1839-1842 (2001).

6. Sarno, S., De Moliner, E., Ruzzene, M., et al. Biochemical and three-dimensional-structural study of the specific inhibition of protein kinase CK2 by [5-oxo-5,6-dihydroindolo-(1,2-a)quinazolin-7-yl]acetic acid (IQA). Biochem. J. 374(Pt 3), 639-646 (2003).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Senna tora (#362788)

Magnoliopsida (#3398)

Anthraquinones from the seeds of Cassia tora with inhibitory activity on protein glycation and aldose reductase.,
Biol Pharm Bull, 2007

Pubmed ID: 17978503

DOI: 10.1248/bpb.30.2207

String Representations

InChiKey (Click to copy)

RHMXXJGYXNZAPX-UHFFFAOYSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C12C(O)=CC(C)=CC=1C(=O)C1=C(C(O)=CC(O)=C1)C2=O

Other Databases

Wikipedia

KEGG ID

HMDB ID

CHEBI ID

PubChem CID

Cayman ID

PDB ID

Calculated Physicochemical Properties

Heavy Atoms 20

Rings 3

Aromatic Rings 2

Rotatable Bonds 0

Van der Waals Molecular Volume 232.01

Topological Polar Surface Area 94.83

Hydrogen Bond Donors 3

Hydrogen Bond Acceptors 5

logP 1.89

Molar Refractivity 69.48

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Created at

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Updated at

19th Apr 2021