EMODIN

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O5
Molecular Weight	270.2369
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3C(=O)C2=C1

InChI

InChIKey=RHMXXJGYXNZAPX-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C15H10O5
Molecular Weight	270.2369
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28831863 | https://www.ncbi.nlm.nih.gov/pubmed/29417945 | https://www.ncbi.nlm.nih.gov/pubmed/29355754

Emodin is a naturally occurring anthraquinone present in the roots of numerous plants and lichens and an active ingredient of various Chinese herbs. Emodin possesses various biological properties and serves as an anti-bacterial and anti-inflammatory agent. Emodin was studied as a potential anti-cancer agent: e.g., it was shown, that compound inhibits the invasion and migration of colon cancer cells in vitro and in vivo by blocking EMT, which is related with the inhibition of Wnt/β-catenin signaling pathway. Besides, emodin effectively ameliorates asthmatic airway inflammation and alternatively activated macrophages (AAMs) polarization, and thus can be a potential agent for the treatment of asthma. It is known that the Inhibition of AAMs is an alternative therapeutic strategy for treating asthma. Some experiments have revealed that emodin can be a beneficial dietary supplement in prolonging lifespan.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Wnt/β-catenin signaling pathway 1 Target ID: Wnt/β-catenin signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/29301594	Modulator 846

Conditions

Condition	Modality	Highest Phase	Product
lung cancer 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29355754	Primary	Basic research	Unknown Approved Use Unknown
Colon cancer 66 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29301594	Primary	Preclinical	Unknown Approved Use Unknown
Asthma 244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29417945	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vitro virucidal activity of selected anthraquinones and anthraquinone derivatives.	1991 Sep	1665961
Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase.	1995 Nov 15	7492599
Cloning and expression of a rat liver phenobarbital-inducible UDP-glucuronosyltransferase (2B12) with specificity for monoterpenoid alcohols.	1995 Oct 1	7574722
Induction of cytochromes P450 1A1 and 1B1 by emodin in human lung adenocarcinoma cell line CL5.	2001 Sep	11502733
Emodin ameliorates glucose-induced matrix synthesis in human peritoneal mesothelial cells.	2003 Aug	12846747
Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context.	2003 Dec	14644660
Transcriptional suppression of the HIV promoter by natural compounds.	2003 Mar	12719011
Neuraminidase inhibitors from Reynoutria elliptica.	2003 May	12785732
Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.	2004 Jan 9	14557274
Antimycobacterial agents from selected Mexican medicinal plants.	2005 Sep	16105233
Bi-directional regulation of emodin and quercetin on smooth muscle myosin of gizzard.	2006 Jan 23	16386736
Emodin inhibits vascular endothelial growth factor-A-induced angiogenesis by blocking receptor-2 (KDR/Flk-1) phosphorylation.	2006 Jun 1	16388516
Inhibition of human cytochrome p450 1b1 further clarifies its role in the activation of dibenzo[a,l]pyrene in cells in culture.	2007	17623886
Emodin and DHA potently increase arsenic trioxide interferon-alpha-induced cell death of HTLV-I-transformed cells by generation of reactive oxygen species and inhibition of Akt and AP-1.	2007 Feb 15	17077332
Identification of kaempferol as an inhibitor of cigarette smoke-induced activation of the aryl hydrocarbon receptor and cell transformation.	2007 Mar	17012224
Emodin induces apoptosis through caspase 3-dependent pathway in HK-2 cells.	2007 Mar 7	17240509
Molecular mechanism of emodin action: transition from laxative ingredient to an antitumor agent.	2007 Sep	17019678
Influence of food polyphenols on aryl hydrocarbon receptor-signaling pathway estimated by in vitro bioassay.	2008 Dec	17869316
Participation of cathepsin B in emodin-induced apoptosis in HK-2 Cells.	2008 Oct 1	18789614
Emodin reverses CCl induced hepatic cytochrome P450 (CYP) enzymatic and ultrastructural changes: The in vivo evidence.	2009 Mar	19067753
Emodin enhances sensitivity of gallbladder cancer cells to platinum drugs via glutathion depletion and MRP1 downregulation.	2010 Apr 15	20005210
Inhibition of ATP-induced macrophage death by emodin via antagonizing P2X7 receptor.	2010 Aug 25	20452342
Inhibition of cytochrome p450 enzymes by quinones and anthraquinones.	2012 Feb 20	22185593
Emodin induces embryonic toxicity in mouse blastocysts through apoptosis.	2012 Sep 4	22609528
Inhibitory effects of herbal constituents on P-glycoprotein in vitro and in vivo: herb-drug interactions mediated via P-gp.	2014 Mar 1	24380838
Emodin Attenuates Cigarette Smoke Induced Lung Injury in a Mouse Model via Suppression of Reactive Oxygen Species Production.	2015 Nov	26139382

Patents

Sample Use Guides

In Vivo Use Guide

murine asthma model: intraperitoneal injection of emodin (20 mg·kg-1·d-1, ip) 1 h prior to DRA (dust mite, ragweed and aspergillus) challenge on days 12-14 significantly decreased pulmonary eosinophil and lymphocyte infiltration, mucus secretion and serum IgE production, as well as IL-4 and IL-5 production in bronchoalveolar lavage fluid.

Route of Administration: Intraperitoneal

In Vitro Use Guide

The potential for emodin to inhibit pancreatic cancer cell proliferation was examined using 4 human pancreatic adenocarcinoma cell lines: Mia Paca-2, BxPC-3, Panc-1, and L3.6pl. Forty-eight-hour treatment with 50 muM emodin inhibited proliferation in Mia Paca-2 cells by 42%, BxPc-3 by 38%, L3.6pl by 56%, and Panc-1 by 18% (all P < .01). In three-fourths of the cell lines, emodin treatment resulted in an increase (from 4.7% to 22%) in the cell population number in apoptosis when measured by flow cytometric analysis

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:55:52 GMT 2025` Edited by `admin` on `Mon Mar 31 17:55:52 GMT 2025`
Record UNII	KA46RNI6HN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-408120

Preferred Name

English

EMODIN

Official Name

English

FRANGULA EMODIN

Common Name

English

RHEUM EMODIN

Common Name

English

EMODOL

Common Name

English

SCHUTTGELB

Common Name

English

NSC-622947

Code

English

EMODIN [MI]

Common Name

English

FRANGULIC ACID

Common Name

English

EMODIN [HSDB]

Common Name

English

1,3,8-TRIHYDROXY-6-METHYL-9,10-ANTHRACENEDIONE

Systematic Name

English

EMODIN [USP-RS]

Common Name

English

ARCHIN

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1967