atromentin (CHEBI:149660)

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ChEBI Name	atromentin

ChEBI ID	CHEBI:149660

Definition	A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxycyclohexa-2,5-diene-1,4-dione which is substituted by a 4-hydroxyphenyl group at positions 3 and 6. It is a mushroom pigment isolated from several fungi species and acts as a smooth muscle stimulant, and exhibits anticoagulant, antibacterial and antineoplastic properties.

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

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Formula

C18H12O6

Net Charge

Average Mass

324.288

Monoisotopic Mass

324.06339

InChI

InChI=1S/C18H12O6/c19-11-5-1-9(2-6-11)13-15(21)17(23)14(18(24)16(13)22)10-3-7-12(20)8-4-10/h1-8,19-21,24H

InChIKey

FKQQKMGWCJGUCS-UHFFFAOYSA-N

SMILES

C1(C(=C(C(C(=C1C2=CC=C(C=C2)O)O)=O)C3=CC=C(C=C3)O)O)=O

Metabolite of Species	Details
Hydnellum diabolus (NCBI:txid176618)	See: PubMed
Clitocybe subilludens (NCBI:txid210149)	Found in cell suspension culture (BTO:0000221). See: PubMed
Clitocybe subilludens (NCBI:txid210149)	See: PubMed
Fungi (NCBI:txid4751)	Found in cell suspension culture (BTO:0000221). Isolated from the solid state fermentation of an unidentified fungus F010248. of strain F010248 See: PubMed
Hypoxylon fendleri (NCBI:txid558530)	Found in cell suspension culture (BTO:0000221). of strain BCC32408 See: PubMed
Hypoxylon fendleri (NCBI:txid558530)	Found in cell suspension culture (BTO:0000221). See: PubMed
Thelephora aurantiotincta (NCBI:txid654496)	Found in fruit body (BTO:0000487). See: PubMed
Paxillus panuoides (NCBI:txid80604)	Identified in the carpophores. See: PubMed

Roles Classification
Biological Role(s):	fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds. EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor An EC 1.3.1.* (oxidoreductase acting on donor CH-CH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of enoyl-[acyl-carrier-protein] reductase (NADH), EC 1.3.1.9. biological pigment An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria.

Application(s):	anticoagulant An agent that prevents blood clotting. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	atromentin (CHEBI:149660) has role antibacterial agent (CHEBI:33282) atromentin (CHEBI:149660) has role anticoagulant (CHEBI:50249) atromentin (CHEBI:149660) has role antineoplastic agent (CHEBI:35610) atromentin (CHEBI:149660) has role apoptosis inducer (CHEBI:68495) atromentin (CHEBI:149660) has role biological pigment (CHEBI:26130) atromentin (CHEBI:149660) has role EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor (CHEBI:139512) atromentin (CHEBI:149660) has role fungal metabolite (CHEBI:76946) atromentin (CHEBI:149660) is a dihydroxy-1,4-benzoquinones (CHEBI:132126) atromentin (CHEBI:149660) is a polyphenol (CHEBI:26195) atromentin (CHEBI:149660) is conjugate acid of atromentin(1−) (CHEBI:149642)

Incoming	atromentin(1−) (CHEBI:149642) is conjugate base of atromentin (CHEBI:149660)

IUPAC Name

3',4,4'',6'-tetrahydroxy[1,1':4',1''-terphenyl]-2',5'-dione

Synonyms	Sources
1⁴,2³,2⁶,3⁴-tetrahydroxy[1¹,2¹:2⁴,3¹-terphenyl]-2²,2⁵-dione	IUPAC
2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)-1,4-benzoquinone	MetaCyc
2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione	ChEBI
2,5-dihydroxy-3,6-bis(p-hydroxyphenyl)-p-benzoquinone	ChemIDplus

Registry Number	Type	Source
519-67-5	CAS Registry Number	ChemIDplus

Last Modified

06 May 2020