5-O-methyl embelin (CHEBI:65842)

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ChEBI Name	5-O-methyl embelin

ChEBI ID	CHEBI:65842

ChEBI ASCII Name	5-O-methyl embelin

Definition	A member of the class of monohydroxy-1,4-benzoquinones that is embelin in which the hydroxy group at position 5 is replaced by a methoxy group. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antileishmanial activity as well as inhibitory activity towards hepatitis C protease.

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

Supplier Information

Download	Molfile XML SDF

Formula

C18H28O4

Net Charge

Average Mass

308.41250

Monoisotopic Mass

308.19876

InChI

InChI=1S/C18H28O4/c1-3-4-5-6-7-8-9-10-11-12-14-17(20)15(19)13-16(22-2)18(14)21/h13,20H,3-12H2,1-2H3

InChIKey

KHBJLRRAMCJZLZ-UHFFFAOYSA-N

SMILES

CCCCCCCCCCCC1=C(O)C(=O)C=C(OC)C1=O

Metabolite of Species	Details
Oxalis erythrorhiza (IPNI:177985-2)	See: PubMed
Embelia schimperi (IPNI:588468-1)	See: PubMed
Lysimachia punctata (NCBI:txid213289)	Found in root (BTO:0001188). Underground part of the plant See: PubMed
Embelia ribes (NCBI:txid459629)	Found in fruit (BTO:0000486). See: PubMed
Embelia ribes (NCBI:txid459629)	Found in leaf (BTO:0000713). See: PubMed
Aegiceras corniculatum (NCBI:txid59970)	Found in stem (BTO:0001300). See: DOI
Aegiceras corniculatum (NCBI:txid59970)	Found in twig (BTO:0001411). See: DOI
Myrsine africana (NCBI:txid59982)	Found in fruit (BTO:0000486). See: ELECTRON J FOOD PLANTS CHEM, 2007, 2, 20

Roles Classification
Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. hepatitis C protease inhibitor An inhibitor of hepatitis C protease, an enzyme required for production of proteins needed for viral assembly. antileishmanial agent An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.

Application(s):	antileishmanial agent An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	5-O-methyl embelin (CHEBI:65842) has functional parent embelin (CHEBI:4778) 5-O-methyl embelin (CHEBI:65842) has role antileishmanial agent (CHEBI:70868) 5-O-methyl embelin (CHEBI:65842) has role antineoplastic agent (CHEBI:35610) 5-O-methyl embelin (CHEBI:65842) has role hepatitis C protease inhibitor (CHEBI:64924) 5-O-methyl embelin (CHEBI:65842) has role metabolite (CHEBI:25212) 5-O-methyl embelin (CHEBI:65842) is a enol ether (CHEBI:47985) 5-O-methyl embelin (CHEBI:65842) is a monohydroxy-1,4-benzoquinones (CHEBI:67273)

IUPAC Name

2-hydroxy-5-methoxy-3-undecylcyclohexa-2,5-diene-1,4-dione

Synonym	Source
2-hydroxy-5-methoxy-3-undecyl-1,4-benzoquinone	ChEBI

Last Modified

03 June 2016

General Comment
2012-07-27	ELECTRON J FOOD PLANTS CHEM, 2007, 2, 20