fosfomycin

CHEBI:28915 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

phosphonic acid antibioticARO:3007149

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:26069 CHEBI:26069
CHEBI:32955 CHEBI:32955
ARO:3007149 ARO:3007149

Chemical structure

Computed structure properties
Molecular formula	C3H7O4P
Charge	0
Average mass	138.059 Da
Monoisotopic mass	138.0082 Da
Source	ChEBI
InChIKey	YMDXZJFXQJVXBF-STHAYSLISA-N

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

Equivalent identifiers for this same structure in other resources.

ARO:0000025
cas:23155-02-4
drugbank:DB00828
drugcentral:1243
kegg.compound:C06454
kegg.drug:D04253
knapsack:C00000789
metacyc.compound:CPD0-1113
pdb-ccd:FCN
reaxys:1680831
chembl:CHEMBL1757
pubchem.compound:73491

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:0000025`	fosfomycin	`antibioticmech:aro-7af65f44e6`	2026-08-30
CHEBI	`CHEBI:28915`	fosfomycin	`antibioticmech:chebi-3102033d1f`	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.

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.)

Resistance mechanisms

48 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_INACTIVATION 33

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
FomA	ARO:3000423	not organism-specific	—	ARO:3000423 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FomB	ARO:3000449	not organism-specific	—	ARO:3000449 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosA	ARO:3000149	not organism-specific	—	ARO:3000149 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosA2	ARO:3002804	not organism-specific	—	ARO:3002804 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosA3	ARO:3002872	not organism-specific	—	ARO:3002872 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosA4	ARO:3003210	not organism-specific	—	ARO:3003210 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosA6	ARO:3004111	not organism-specific	—	ARO:3004111 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosA7	ARO:3004113	not organism-specific	—	ARO:3004113 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosA7.5	ARO:3005162	not organism-specific	—	ARO:3005162 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosA8	ARO:3007371	not organism-specific	—	ARO:3007371 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosB	ARO:3000172	not organism-specific	—	ARO:3000172 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosB1	ARO:3004670	not organism-specific	—	ARO:3004670 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosB2	ARO:3005100	not organism-specific	—	ARO:3005100 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosB3	ARO:3002873	not organism-specific	—	ARO:3002873 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosB4	ARO:3004671	not organism-specific	—	ARO:3004671 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosB5	ARO:3004672	not organism-specific	—	ARO:3004672 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosB6	ARO:3004673	not organism-specific	—	ARO:3004673 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosBx1	ARO:3007372	not organism-specific	—	ARO:3007372 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosC	ARO:3000380	not organism-specific	—	ARO:3000380 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosC2	ARO:3002874	not organism-specific	—	ARO:3002874 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosD	ARO:3004674	not organism-specific	—	ARO:3004674 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosG	ARO:3007368	not organism-specific	—	ARO:3007368 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosH	ARO:3007369	not organism-specific	—	ARO:3007369 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosI	ARO:3007370	not organism-specific	—	ARO:3007370 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosK	ARO:3003207	not organism-specific	—	ARO:3003207 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosL1	ARO:3005024	not organism-specific	—	ARO:3005024 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosM1	ARO:3007097	not organism-specific	—	ARO:3007097 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosM2	ARO:3007098	not organism-specific	—	ARO:3007098 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosM3	ARO:3007099	not organism-specific	—	ARO:3007099 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosX	ARO:3000198	not organism-specific	—	ARO:3000198 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosXCC	ARO:3003208	not organism-specific	—	ARO:3003208 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
FosY	ARO:3007069	not organism-specific	—	ARO:3007069 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
Staphylococcus aureus FosB	ARO:3004661	not organism-specific	—	ARO:3004661 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 12

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Borreliella burgdorferi murA with mutation conferring resistance to fosfomycin	ARO:3003777	not organism-specific	—	ARO:3003777 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
Chlamydia trachomatis intrinsic murA conferring resistance to fosfomycin	ARO:3003785	not organism-specific	—	ARO:3003785 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
Escherichia coli GlpT with mutation conferring resistance to fosfomycin	ARO:3003889	not organism-specific	—	ARO:3003889 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
Escherichia coli PtsI with mutation conferring resistance to fosfomycin	ARO:3003899	not organism-specific	—	ARO:3003899 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
Escherichia coli UhpT with mutation conferring resistance to fosfomycin	ARO:3003890	not organism-specific	—	ARO:3003890 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
Escherichia coli cyaA with mutation conferring resistance to fosfomycin	ARO:3003900	not organism-specific	—	ARO:3003900 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
Escherichia coli murA with mutation conferring resistance to fosfomycin	ARO:3003775	not organism-specific	—	ARO:3003775 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
Escherichia coli uhpA with mutation conferring resistance to fosfomycin	ARO:3003893	not organism-specific	—	ARO:3003893 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
Mycobacterium tuberculosis intrinsic murA conferring resistance to fosfomycin	ARO:3003784	not organism-specific	—	ARO:3003784 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
Staphylococcus aureus GlpT with mutation conferring resistance to fosfomycin	ARO:3003901	not organism-specific	—	ARO:3003901 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
Staphylococcus aureus UhpT with mutation conferring resistance to fosfomycin	ARO:3003902	not organism-specific	—	ARO:3003902 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
Staphylococcus aureus murA with mutation conferring resistance to fosfomycin	ARO:3003776	not organism-specific	—	ARO:3003776 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 2

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Acinetobacter baumannii AbaF	ARO:3004573	not organism-specific	—	ARO:3004573 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)
mdtG	ARO:3001329	not organism-specific	—	ARO:3001329 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_PROTECTION 1

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
msr(I)	ARO:3007043	not organism-specific	—	ARO:3007043 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000025 (fosfomycin); database assertion, not a primary citation.)

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

Provenance

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