fosmidomycin (CHEBI:443725)

CHEBI:443725 - fosmidomycin

ChEBI ID	CHEBI:443725
ChEBI Name	fosmidomycin
Stars
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.
Secondary ChEBI ID	CHEBI:42526
Last Modified	11 March 2014
Downloads	Molfile

Formula	C4H10NO5P
Net Charge	0
Average Mass	183.100
Monoisotopic Mass	183.02966
SMILES	O=CN(O)CCCP(=O)(O)O
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

Roles Classification

bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria.

antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.

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).

ChEBI Ontology

Outgoing Relation(s)
	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

Manual Xrefs	Databases
FOM	PDBeChem
DB02948	DrugBank

Registry Numbers	Sources
Reaxys:4133006	Reaxys
CAS:66508-53-0	ChemIDplus

Citations