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CHEBI:65931 - fumimycin

ChEBI IDCHEBI:65931
ChEBI Namefumimycin
Stars
DefinitionA member of the class of 1-benzofurans that is 1-benzofuran-2(3H)-one substituted by a propenyl group at position 4, hydroxy groups at positions 5 and 6, methyl group at position 3 and a [(2E)-3-carboxyprop-2-enoyl]nitrilo group at position 3. Isolated from the fermentation broth of Aspergillus fumisynnematus F746, it exhibits antibacterial activity.
Last Modified5 March 2014
DownloadsMolfile
FormulaC16H15NO7
Net Charge0
Average Mass333.296
Monoisotopic Mass333.08485
SMILESC/C=C/c1c(O)c(O)cc2c1[C@@](C)(NC(=O)/C=C/C(=O)O)C(=O)O2
InChIInChI=1S/C16H15NO7/c1-3-4-8-13-10(7-9(18)14(8)22)24-15(23)16(13,2)17-11(19)5-6-12(20)21/h3-7,18,22H,1-2H3,(H,17,19)(H,20,21)/b4-3+,6-5+/t16-/m1/s1
InChIKeyQWMZGLCXYLPQAZ-CJWQODIFSA-N
Species of MetaboliteComponentSourceComments
Aspergillus fumisynnematus (ncbitaxon:286432) - PubMed (17523650) Strain: F746
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
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 3.5.1.88 (peptide deformylase) inhibitor  An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the action of peptide deformylase (EC 3.5.1.88), involved in the catalytic removal of the N-terminal formyl group of nascent proteins.
ChEBI Ontology
Outgoing Relation(s)
fumimycin (CHEBI:65931) has role Aspergillus metabolite (CHEBI:76956)
fumimycin (CHEBI:65931) has role antibacterial agent (CHEBI:33282)
fumimycin (CHEBI:65931) has role EC 3.5.1.88 (peptide deformylase) inhibitor (CHEBI:71951)
fumimycin (CHEBI:65931) is a 1-benzofurans (CHEBI:38830)
fumimycin (CHEBI:65931) is a dicarboxylic acid monoamide (CHEBI:35735)
fumimycin (CHEBI:65931) is a monocarboxylic acid (CHEBI:25384)
fumimycin (CHEBI:65931) is a polyphenol (CHEBI:26195)
fumimycin (CHEBI:65931) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(2E)-4-({(3R)-5,6-dihydroxy-3-methyl-2-oxo-4-[(1E)-prop-1-en-1-yl]-2,3-dihydro-1-benzofuran-3-yl}amino)-4-oxobut-2-enoic acid
Manual XrefsDatabases
20557857ChemSpider
Registry NumbersSources
Reaxys:21037523Reaxys
Citations