fosmidomycin

CHEBI:443725 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

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.

Label unavailable CHEBI:24650
Label unavailable CHEBI:26069
phosphonic acid antibiotic 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

drugbank:DB02948

Activity roles

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

antimicrobial agent 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.)

1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR) PROTEIN DIRECT_BINDING_TARGET

A 2.2-angstrom E. coli DXR quaternary crystal structure contained fosmidomycin, Mg2+, and NADPH and ordered the flexible active-site loop. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2007-05 (retrieved 2026-09-02).

Escherichia coli NCBITaxon:562

Organism-specific examples
Protein	Gene	Organism	Entry
1-deoxy-D-xylulose 5-phosphate reductoisomerase `UniProtKB:P45568` Non-mevalonate isoprenoid pathway enzyme crystallized in a ternary complex with NADPH and fosmidomycin in E. coli (PMID:17554164; K-12 reference strain context).	dxr	Escherichia coli (strain K12) `NCBITaxon:83333`	REVIEWED

PMID:17554164 (Primary fosmidomycin-DXR-Mg2+-NADPH structure (DOI:10.1107/S1744309107024475).)

Mechanism summary

Mode of action: OTHER microbial target — CURATOR: PMID:17554164 resolved fosmidomycin with Escherichia coli 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), Mg2+, and NADPH at 2.2 angstrom. DXR catalyzes the MEP/non-mevalonate pathway of isoprenoid biosynthesis; the schema has no dedicated isoprenoid-pathway mechanism, so the reviewed coarse mode remains OTHER rather than forcing a false bucket.

Record-level evidence

PMID:17554164 (Primary exact-fosmidomycin DXR quaternary-complex structure.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
REVIEWED 2026-09-03 · codex · LLM-assisted
Verified exact ChEBI/CARD identity, structure, antibacterial role, class, and retained CARD target provenance; added the directly observed DXR target and recorded the absent coarse isoprenoid-pathway enum as an explicit gap.
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_UNIPROT_PROTEIN_EXAMPLES 2026-10-18 · antigravity · LLM-assisted
Added curated E. coli K-12 DXR (P45568) UniProtKB protein example on the PRIMARY_LITERATURE 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR) molecular target.

Provenance

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

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