Fosmidomycin

Fosmidomycin
Clinical data
ATC code	none;
Identifiers
	IUPAC name 3-[Formyl(hydroxy)amino]propylphosphonic acid;
CAS Number	66508-53-0 ;
PubChem CID	572;
DrugBank	DB02948 ;
ChemSpider	555 ;
UNII	5829E3D9I9;
ChEBI	CHEBI:443725 ;
ChEMBL	ChEMBL203125 ;
CompTox Dashboard (EPA)	DTXSID70216712 ;
Chemical and physical data
Formula	C4H10NO5P
Molar mass	183.100 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=P(O)(O)CCCN(O)C=O;
	InChI InChI=1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10) ; Key:GJXWDTUCERCKIX-UHFFFAOYSA-N ;
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Fosmidomycin is an antibiotic that was originally isolated from culture broths of bacteria of the genus Streptomyces. It specifically inhibits DXP reductoisomerase, a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis. It is a structural analogue of 2-C-methyl-D-erythrose 4-phosphate. It inhibits the E. coli enzyme with a KI value of 38 nM (4), MTB at 80 nM, and the Francisella enzyme at 99 nM. Several mutations in the E. coli DXP reductoisomerase were found to confer resistance to fosmidomycin.

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