fumimycin (CHEBI:65931)

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ChEBI Name	fumimycin

ChEBI ID	CHEBI:65931

Definition	A 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.

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

Supplier Information

Download	Molfile XML SDF

Formula

C16H15NO7

Net Charge

Average Mass

333.29280

Monoisotopic Mass

333.08485

InChI

InChI=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

InChIKey

QWMZGLCXYLPQAZ-CJWQODIFSA-N

SMILES

C\C=C\c1c(O)c(O)cc2OC(=O)[C@](C)(NC(=O)\C=C\C(O)=O)c12

Metabolite of Species	Details
Aspergillus fumisynnematus (NCBI:txid286432)	of strain F746 See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus . antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. 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	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 γ-lactone (CHEBI:37581) 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)

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

Registry Number	Type	Source
21037523	Reaxys Registry Number	Reaxys

Last Modified

05 March 2014