terreic acid (CHEBI:156546)

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This entity has been annotated by a third party. If you would like more information added to this entry, please contact ChEBI via email or GitHub.

ChEBI Name	terreic acid

ChEBI ID	CHEBI:156546

Definition	A 2-hydroxy-1,4-benzoquinone that is 5,6-epoxy. It is a natural product of Aspergillus terreus. It has an antibacterial activity explained by its inhibitory effect on bacterial enzymes MurA and GlmU. It is an inhibitor of Bruton's tyrosine kinase, and has an anti-tumoral activity against HeLa and EAC cells.

Stars	This entity has been manually annotated by a third party.

Submitter	Martin Larralde

Supplier Information

Download	Molfile XML SDF

Formula

C7H6O4

Net Charge

Average Mass

154.121

Monoisotopic Mass

154.02661

InChI

InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1

InChIKey

ATFNSNUJZOYXFC-RQJHMYQMSA-N

SMILES

CC1=C(C([C@H]2[C@@H](C1=O)O2)=O)O

Metabolite of Species	Details
Aspergillus terreus NIH2624 (NCBI:txid341663)	See: PubMed

Roles Classification
Biological Role(s):	mycotoxin Poisonous substance produced by fungi. antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of UDP-N-acetylglucosamine 1-carboxyvinyltransferase (EC 2.5.1.7). EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor An EC 2.3.* (acyltransferase) inhibitor that inhibits the action of any acyltransferase transferring groups other than amino-acyl groups (EC 2.3.1.). EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor An EC 2.7.10. (protein-tyrosine kinase) inhibitor that specifically blocks the action of non-specific protein-tyrosine kinase (EC 2.7.10.2). Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .

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

ChEBI Ontology
Outgoing	terreic acid (CHEBI:156546) has functional parent 2-hydroxy-1,4-benzoquinone (CHEBI:18400) terreic acid (CHEBI:156546) has role Aspergillus metabolite (CHEBI:76956) terreic acid (CHEBI:156546) has role antibacterial agent (CHEBI:33282) terreic acid (CHEBI:156546) has role antineoplastic agent (CHEBI:35610) terreic acid (CHEBI:156546) has role EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor (CHEBI:76878) terreic acid (CHEBI:156546) has role EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor (CHEBI:78379) terreic acid (CHEBI:156546) has role EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor (CHEBI:76617) terreic acid (CHEBI:156546) has role mycotoxin (CHEBI:25442) terreic acid (CHEBI:156546) is a arene epoxide (CHEBI:37410) terreic acid (CHEBI:156546) is a diketone (CHEBI:46640) terreic acid (CHEBI:156546) is a monohydroxy-1,4-benzoquinones (CHEBI:67273) terreic acid (CHEBI:156546) is a tertiary α-hydroxy ketone (CHEBI:139592)

IUPAC Name

(1R,6S)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

Registry Number	Type	Source
121-40-4	CAS Registry Number	ChemIDplus

Last Modified

28 September 2020