fosmidomycin (CHEBI:443725)

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ChEBI Name	fosmidomycin

ChEBI ID	CHEBI:443725

Definition	Propylphosphonic acid in which one of the hydrogens at position 3 is substituted by a formyl(hydroxy)amino group. An antibiotic obtained from Streptomyces lavendulae, it specifically inhibits DXP reductoisomerase (EC 1.1.1.267), a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis.

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

Secondary ChEBI IDs	CHEBI:42526

Supplier Information

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Formula

C4H10NO5P

Net Charge

Average Mass

183.09970

Monoisotopic Mass

183.02966

InChI

InChI=1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10)

InChIKey

GJXWDTUCERCKIX-UHFFFAOYSA-N

SMILES

ON(CCCP(O)(O)=O)C=O

Roles Classification
Biological Role(s):	bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. EC 1.1.1.267 (1-deoxy-D-xylulose-5-phosphate reductoisomerase) inhibitor An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of 1-deoxy-D-xylulose-5-phosphate reductoisomerase (EC 1.1.1.267). antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.

ChEBI Ontology
Outgoing	fosmidomycin (CHEBI:443725) has role antimicrobial agent (CHEBI:33281) fosmidomycin (CHEBI:443725) has role bacterial metabolite (CHEBI:76969) fosmidomycin (CHEBI:443725) has role EC 1.1.1.267 (1-deoxy-D-xylulose-5-phosphate reductoisomerase) inhibitor (CHEBI:77654) fosmidomycin (CHEBI:443725) is a hydroxamic acid (CHEBI:24650) fosmidomycin (CHEBI:443725) is a phosphonic acids (CHEBI:26069)

IUPAC Name

{3-[formyl(hydroxy)amino]propyl}phosphonic acid

Synonym	Source
3-(N-hydroxyformamido)propylphosphonic acid	ChEMBL

Last Modified

11 March 2014