CHEBI:443725 - fosmidomycin

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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 0
Average Mass 183.09970
Monoisotopic Mass 183.030
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.
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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
INNs Sources
fosmidomycin ChemIDplus
fosmidomycina ChemIDplus
fosmidomycine ChemIDplus
fosmidomycinum ChemIDplus
Synonym Source
3-(N-hydroxyformamido)propylphosphonic acid ChEMBL
Database Links Databases
DB02948 DrugBank
FOM PDBeChem
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Registry Numbers Types Sources
4133006 Reaxys Registry Number Reaxys
66508-53-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15339150 PubMed citation Europe PMC
16439126 PubMed citation ChEMBL
16610809 PubMed citation ChEMBL
17149863 PubMed citation ChEMBL
17583502 PubMed citation ChEMBL
18158249 PubMed citation ChEMBL
Last Modified
11 March 2014