EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:443725 - fosmidomycin

Default Structure
ChEBI IDCHEBI:443725
ChEBI Namefosmidomycin
Stars
DefinitionPropylphosphonic 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.
Secondary ChEBI IDCHEBI:42526
Last Modified11 March 2014
DownloadsMolfile
FormulaC4H10NO5P
Net Charge0
Average Mass183.100
Monoisotopic Mass183.02966
SMILESO=CN(O)CCCP(=O)(O)O
InChIInChI=1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10)
InChIKeyGJXWDTUCERCKIX-UHFFFAOYSA-N
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
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).
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application:
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
ChEBI Ontology
Outgoing Relation(s)
fosmidomycin (CHEBI:443725) has role antimalarial (CHEBI:38068)
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  Source
fosmidomicinaWHO MedNet
fosmidomycinChemIDplus
fosmidomycinaChemIDplus
fosmidomycineChemIDplus
fosmidomycinumChemIDplus
Synonym  Source
3-(N-hydroxyformamido)propylphosphonic acidChEMBL
Manual XrefsDatabases
DB02948DrugBank
FOMPDBeChem
Registry NumbersSources
Reaxys:4133006Reaxys
CAS:66508-53-0ChemIDplus
Citations