fosfomycin

CHEBI:28915 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus. — ChEBI

Classification

phosphonic acid antibioticARO:3007149

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:26069
• Label unavailable CHEBI:32955
• phosphonic acid antibiotic ARO:3007149

Chemical structure

SMILES

C[C@@H]1O[C@@H]1P(=O)(O)O

InChI

InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1

Also called

• fosfomicina (INN)— chebi
• fosfomycine (INN)— chebi
• fosfomycinum (INN)— chebi
• [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid (EXACT_SYNONYM)— chebi
• (-)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid (EXACT_SYNONYM)— chebi
• (1R,2S)-epoxypropylphosphonic acid (EXACT_SYNONYM)— chebi
• (2R-cis)-(3-Methyloxiranyl)phosphonic acid (EXACT_SYNONYM)— chebi
• 1R-cis-(1,2-epoxypropyl)phosphonic acid (EXACT_SYNONYM)— chebi
• FCM (EXACT_SYNONYM)— chebi
• FOSFOMYCIN (EXACT_SYNONYM)— chebi
• L-cis-1,2-epoxypropylphosphonic acid (EXACT_SYNONYM)— chebi
• Phosphomycin (EXACT_SYNONYM)— chebi
• Phosphonomycin (EXACT_SYNONYM)— chebi
• cis-(1R,2S)-epoxypropylphosphonic acid (EXACT_SYNONYM)— chebi
• phosphonemycin (EXACT_SYNONYM)— chebi
• (1R,2S)-1,2-epoxy-propylphosphonic acid (EXACT_SYNONYM)— aro
• phosphomycin (EXACT_SYNONYM)— aro
• phosphonomycin (EXACT_SYNONYM)— aro

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.

• fosfomycinARO:0000025
• cas:23155-02-4
• kegg.compound:C06454
• knapsack:C00000789
• pdb-ccd:FCN
• reaxys:1680831
• chembl:CHEMBL1757
• pubchem.compound:73491

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:DB00828
• drugcentral:1243
• kegg.drug:D04253

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.

Related pathway records

Evidence-qualified relationships to a pinned corpus revision.

PathwayMech: WikiPathways:WP5060TARGETS_PATHWAY_COMPONENT
PMID:8994972 establishes the E. coli MurA–fosfomycin complex. The linked E. coli pathway contains MurA (UniProtKB:P0A749); this links the target to its pathway, not the drug to every step.
Source revision: aa305727458c44ab05614901334540e2c87a9f3a

Molecular targets

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

fosfomycin sensitive pyruvyl transferase (murA) PROTEIN DIRECT_BINDING_TARGET

ARO:3000724

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

• ARO:3000724 (CARD/ARO asserts targeted_by_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)

UDP-N-acetylglucosamine enolpyruvyl transferase (MurA) PROTEIN DIRECT_BINDING_TARGET

A 1.8-angstrom E. coli MurA cocrystal directly showed fosfomycin covalently bound to active-site Cys115 alongside UDP-GlcNAc. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 1996-12 (retrieved 2026-09-02).

Escherichia coli NCBITaxon:562

• PMID:8994972 (Primary fosfomycin-MurA cocrystal (DOI:10.1016/S0969-2126(96)00153-0).)

Mechanism summary

Mode of action

CELL_WALL_SYNTHESIS_INHIBITION microbial target — CURATOR: PMID:8994972 resolved fosfomycin and UDP-N-acetylglucosamine in a 1.8-angstrom Escherichia coli MurA complex. Fosfomycin was covalently attached to Cys115, inhibiting the first committed step of bacterial peptidoglycan biosynthesis.

Resistance mechanisms

48 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

Producer organisms

Organisms that biosynthesize this compound. Cluster link evidence is how the upstream source graded the gene cluster, so it is populated only for a source that grades it. An empty cell is not weaker support: a curator-authored producer carries its support in Evidence instead. Where the source entry named several compounds, the evidence is marked inherited, meaning it covers this compound together with the cluster's other products rather than singling it out. Those products need not be related to each other: a cluster can list an intermediate, a precursor and a finished antibiotic side by side.

Record-level evidence

• PMID:8994972 (Primary exact-fosfomycin MurA cocrystal and peptidoglycan-pathway study.)

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

5. REVIEWED 2026-09-03 · codex · LLM-assisted

   Verified exact ChEBI/CARD identity, structure, antibiotic role, class, and provenance of retained CARD target and 48 resistance assertions; added cell-wall synthesis inhibition and the directly observed covalent MurA target.

6. RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

7. RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

8. RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

9. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

10. ADD_PATHWAY_LINKS 2026-10-05 · codex · LLM-assisted

    Added reviewed PathwayMech relationships and any supported protein example from curation/pathway_links.yaml; organism and evidence limits are recorded in each basis.

Provenance

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

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