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CHEBI:156546 - terreic acid

ChEBI IDCHEBI:156546
ChEBI Nameterreic acid
Stars
DefinitionA 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.
Last Modified28 September 2020
SubmitterMartin Larralde
DownloadsMolfile
FormulaC7H6O4
Net Charge0
Average Mass154.121
Monoisotopic Mass154.02661
SMILESCC1=C(O)C(=O)[C@@H]2O[C@@H]2C1=O
InChIInChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1
InChIKeyATFNSNUJZOYXFC-RQJHMYQMSA-N
Species of MetaboliteComponentSourceComments
Aspergillus terreus NIH2624 (ncbitaxon:341663) - PubMed (25265334)
Roles Classification
Biological Roles:
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
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).
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.*).
mycotoxin  Poisonous substance produced by fungi.
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).
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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)
terreic acid (CHEBI:156546) is conjugate acid of terreate (CHEBI:233617)
Incoming Relation(s)
terreate (CHEBI:233617) is conjugate base of terreic acid (CHEBI:156546)
IUPAC Name 
(1R,6S)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
Manual XrefsDatabases
C00018689KNApSAcK
Registry NumbersSources
CAS:121-40-4ChemIDplus
Citations