Structure Database (LMSD)

Common Name
Aloe-emodin
Systematic Name
1,8-dihydroxy-3-(hydroxymethyl)-9,10-anthracenedione
Synonyms
  • 3-Hydroxymethylchrysazine
  • Rhabarberone
LM ID
LMPK13040002
Formula
Exact Mass
Calculate m/z
270.052825
Status
Curated



Classification

Biological Context

Aloe-emodin is a hydroxyanthraquinone found in Aloe vera leaves that has potent laxative action by inducing chloride secretion in colonic mucosa and releasing acetylcholine, which stimulates contraction of intestinal smooth muscle.1 It also demonstrates anti-tumor activity (ED50s = 1-13 µM), inducing apoptosis in various cancer cells by increasing the production of reactive oxygen species.2,3 Aloe-emodin is reported to have estrogenic activity as a phytoestrogen and has been shown to inhibit breast cancer cell proliferation by downregulating ERα protein levels, and thus, suppressing transcriptional activation of the receptor.4,5

This information has been provided by Cayman Chemical

References

1. 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).
3. Xie, M.J., Ma, Y.H., Miao, L., et al. Emodin-provoked oxidative stress induces apoptosis in human colon cancer HCT116 cells through a p53-mitochondrial apoptotic pathway. Asian Pac. J. Cancer Prev. 15(13), 5201-5205 (2014).
4. Pecere, T., Gazzola, M.V., Mucignat, C., et al. Aloe-emodin is a new type of anticancer agent with selective activity against neuroectodermal tumors. Cancer Res. 60(11), 2800-2804 (2000).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Aloe vera (#34199)
Magnoliopsida (#3398)
The compounds in Aloe leaf exudates: a review,
Botan J, 2008

String Representations

InChiKey (Click to copy)
YDQWDHRMZQUTBA-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-1-3-10(12)17/h1-5,16-18H,6H2
SMILES (Click to copy)
C12C=C(C=C(O)C=1C(=O)C1=C(C=CC=C1O)C2=O)CO

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 3
Aromatic Rings 2
Rotatable Bonds 1
Van der Waals Molecular Volume 232.01
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 1.37
Molar Refractivity 69.00

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Created at
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Updated at
19th Sep 2023