emodin (CHEBI:42223)

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ChEBI Name	emodin

ChEBI ID	CHEBI:42223

Definition	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.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:42221, CHEBI:4782

Supplier Information	ChemicalBook:CB2258856, eMolecules:509347, Selleckchem:Emodin, ZINC000003824868

Download	Molfile XML SDF

Wikipedia	License
Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is an organic compound. Classified as an anthraquinone, it can be isolated from rhubarb, buckthorn, and Japanese knotweed (Reynoutria japonica syn. Polygonum cuspidatum). Emodin is particularly abundant in the roots of the Chinese rhubarb (Rheum palmatum), knotweed and knotgrass (Polygonum cuspidatum and Polygonum multiflorum) as well as Hawaii ‘au‘auko‘i cassia seeds or coffee weed (Semen cassia). It is specifically isolated from Rheum palmatum L. It is also produced by many species of fungi, including members of the genera Aspergillus, Pyrenochaeta, and Pestalotiopsis, inter alia. The common name is derived from Rheum emodi, a taxonomic synonym of Rheum australe (Himalayan rhubarb), and synonyms include emodol, frangula emodin, rheum emodin, 3-methyl-1,6,8-trihydroxyanthraquinone, Schüttgelb (Schuttgelb), and Persian Berry Lake.
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Formula

C15H10O5

Net Charge

Average Mass

270.23690

Monoisotopic Mass

270.05282

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

SMILES

Cc1cc(O)c2C(=O)c3c(O)cc(O)cc3C(=O)c2c1

Metabolite of Species	Details
Microdiplodia (NCBI:txid371130)	EtOAc extract of an endophytic fungi isolated from Lycium intricatum of strain 9907 See: PubMed

Roles Classification
Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. tyrosine kinase inhibitor Any protein kinase inhibitor that interferes with the action of tyrosine kinase.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. laxative An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.

ChEBI Ontology
Outgoing	emodin (CHEBI:42223) has functional parent emodin anthrone (CHEBI:150013) emodin (CHEBI:42223) has role antineoplastic agent (CHEBI:35610) emodin (CHEBI:42223) has role laxative (CHEBI:50503) emodin (CHEBI:42223) has role plant metabolite (CHEBI:76924) emodin (CHEBI:42223) has role tyrosine kinase inhibitor (CHEBI:38637) emodin (CHEBI:42223) is a trihydroxyanthraquinone (CHEBI:37488) emodin (CHEBI:42223) is conjugate acid of emodin(1−) (CHEBI:77659)

Incoming	isoskyrin (CHEBI:144065) has functional parent emodin (CHEBI:42223) questin (CHEBI:16200) has functional parent emodin (CHEBI:42223) skyrin (CHEBI:144311) has functional parent emodin (CHEBI:42223) emodin(1−) (CHEBI:77659) is conjugate base of emodin (CHEBI:42223)

IUPAC Name

1,3,8-trihydroxy-6-methylanthra-9,10-quinone

Synonyms	Sources
1,3,8-trihydroxy-6-methyl-9,10-anthracenedione	ChemIDplus
1,3,8-trihydroxy-6-methyl-9,10-anthraquinone	ChemIDplus
3-METHYL-1,6,8-TRIHYDROXYANTHRAQUINONE	PDBeChem
Emodin	KEGG COMPOUND
Schuttgelb	ChemIDplus

Citations

Last Modified

26 May 2020