AntibioticMech

fosmidomycin

CHEBI:443725 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Classification

phosphonic acid antibioticARO:3007149

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:24650 CHEBI:24650
• CHEBI:26069 CHEBI:26069
• ARO:3007149 ARO:3007149

Chemical structure

Computed structure properties

Molecular formula	C4H10NO5P
Charge	0
Average mass	183.1 Da
Monoisotopic mass	183.02966 Da
Source	ChEBI
InChIKey	GJXWDTUCERCKIX-UHFFFAOYSA-N

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)

Also called

• fosmidomycina (INN)— chebi
• fosmidomycine (INN)— chebi
• fosmidomycinum (INN)— chebi
• {3-[formyl(hydroxy)amino]propyl}phosphonic acid (EXACT_SYNONYM)— chebi
• 3-(N-hydroxyformamido)propylphosphonic acid (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3000758
• cas:66508-53-0
• drugbank:DB02948
• pdb-ccd:FOM
• reaxys:4133006
• chembl:CHEMBL203125
• pubchem.compound:572

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

• CHEBI:33281 CHEBI:33281

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record

Source	Native ID	Label	Minted CURIE	Version
ARO	ARO:3000758	fosmidomycin	antibioticmech:aro-ec2610057a	2026-08-30
CHEBI	CHEBI:443725	fosmidomycin	antibioticmech:chebi-b17da11f5c	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

1-deoxy-D-xylulose 5-phosphate reductoisomerase PROTEIN DIRECT_BINDING_TARGET

ARO:3000743

CARD/ARO database assertion; target organism, strain, and assay are not specified. DXR is asserted as the enzyme target. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

• ARO:3000743 (CARD/ARO asserts targeted_by_antibiotic ARO:3000758 (fosmidomycin); database assertion, not a primary citation.)

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.