Fosfomycin (CED0002348)

Record Information
Version1.0
Creation Date2016-05-25 18:23:10 UTC
Update Date2026-08-22 13:44:17 UTC
Accession NumberCHEM022190
Identification
Common NameFosfomycin
ClassSmall Molecule
Description
Fosfomycin is an organic compound with the chemical formula C3H7O4P and an average molecular weight of 138.06 g/mol. Fosfomycin belongs to the organic phosphonic acids, a subclass of organic phosphonic acids and derivatives within the organic compounds. In terms of biological activity, it acts as an inhibitor of the protein target UDP-N-acetylglucosamine 1-carboxyvinyltransferase (murA). The compound is found in or released from eight recorded sources. These include pharmaceuticals and veterinary products, specifically antibiotics, antiinfectives, and antibacterials. It is also associated with food, food processing and cookware, specifically processing meats, as well as household cleaning and consumer products, such as non electric simulated smoking devices. Additionally, it is found in electrical and electronic equipment, including television systems, antennas, and video games. Recorded exposure routes for fosfomycin include oral, intravenous, and inhalation.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acidChEBI
(1R,2S)-Epoxypropylphosphonic acidChEBI
(2R-cis)-(3-Methyloxiranyl)phosphonic acidChEBI
1R-cis-(1,2-Epoxypropyl)phosphonic acidChEBI
cis-(1R,2S)-Epoxypropylphosphonic acidChEBI
FCMChEBI
FosfomicinaChEBI
FosfomycineChEBI
FosfomycinumChEBI
L-cis-1,2-Epoxypropylphosphonic acidChEBI
PhosphomycinChEBI
PhosphonemycinChEBI
PhosphonomycinChEBI
(1R,2S)-EpoxypropylphosphonateKegg
(-)-(1R,2S)-(1,2-Epoxypropyl)phosphonateGenerator
(2R-cis)-(3-Methyloxiranyl)phosphonateGenerator
1R-cis-(1,2-Epoxypropyl)phosphonateGenerator
cis-(1R,2S)-EpoxypropylphosphonateGenerator
L-cis-1,2-EpoxypropylphosphonateGenerator
FosfocinaHMDB
Fosfomycin disodium saltHMDB
Fosfomycin sodiumHMDB
FosfonomycinHMDB
Phosphomycin disodium saltHMDB
Fosfomycin tromethamineHMDB
Fosfomycin trometamol saltHMDB
Tromethamine, fosfomycinHMDB
MonurilHMDB
Chemical FormulaC3H7O4P
Average Molecular Mass138.059 g/mol
Monoisotopic Mass138.008 g/mol
CAS Registry Number23155-02-4
IUPAC Name[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
Traditional Namefosfomycin
SMILESC[C@@H]1O[C@@H]1P(O)(O)=O
InChI IdentifierInChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
InChI KeyYMDXZJFXQJVXBF-STHAYSLISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphonic acids and derivatives
Sub ClassOrganic phosphonic acids
Direct ParentOrganic phosphonic acids
Alternative Parents
Substituents
  • Organophosphonic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Oxirane
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility46.9 g/LALOGPS
logP-0.86ALOGPS
logP-0.74ChemAxon
logS-0.47ALOGPS
pKa (Strongest Acidic)1.25ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.87 m³·mol⁻¹ChemAxon
Polarizability10.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-03di-2980000000-005d5b96a1e9219362d0Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-03di-2980000000-005d5b96a1e9219362d0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-003r-9100000000-f3dc2512a6ad53fb9238Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-1900000000-3025442157ee47184674Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9100000000-275a01dd7f8cc74a7b6fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9100000000-859fa61894a0825e23d2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-3900000000-22234a977a4d3da18ecfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05qi-9500000000-81b95429a7694bba36c7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-057i-9000000000-d2dbdb85a43ce508ab14Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-2900000000-3865d3126791b7f8f8f3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000b-9400000000-d43f705d0ad2bb7e25c9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06tn-9000000000-5460c55de4fe7bea9b0dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dr-9400000000-f59b9b60406eacd3c3daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03fr-9000000000-eb71c23b854ab0f65f4aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9000000000-987956f210941d36e458Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2439.0Log mg/kg[1400:4300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
cystitisis_treatment_forNot AvailablePMC10816374
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
347AntibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
395AntiinfectivesHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
552Processing MeatsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
630ToysRecreation & sports surfacesNot Available
643HeadwearTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Fosfomycin Drug Metabolism Action Pathway
Fosfomycin Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureInositol 1,4,5-trisphosphate-gated calcium channel ITPR3Q8WN95Bos taurusPredicted (SEA)1.32344
N-acetylglucosamine-6-phosphate deacetylase structureClick to view 3D structureN-acetylglucosamine-6-phosphate deacetylaseQ9Y303HumansPredicted (SEA)7.94062
Click to view 3D structureType IV secretion-like conjugative transfer relaxase protein TraIB1LRJ1Escherichia coli (strain SMS-3-5 / SECEC)Predicted (SEA)0.778492
Click to view 3D structureInositol-trisphosphate 3-kinase AP17105Rattus norvegicusPredicted (SEA)1.32344
Click to view 3D structureInositol 1,4,5-trisphosphate-gated calcium channel ITPR1P29994Rattus norvegicusPredicted (SEA)3.65891
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)4663.79
Inositol 1,4,5-trisphosphate-gated calcium channel ITPR3 structureClick to view 3D structureInositol 1,4,5-trisphosphate-gated calcium channel ITPR3Q14573HumansPredicted (SEA)1.71268
Click to view 3D structureType 1 InsP3 receptor isoform S2P79248Sus scrofaPredicted (SEA)1.47914
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)4325.93
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)4113.86
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)4389.76
Click to view 3D structure1-deoxy-D-xylulose-5-phosphate synthaseB7UJP3Escherichia coli O127:H6 (strain E2348/69 / EPEC)Predicted (SEA)10.3539
Click to view 3D structureInositol 1,4,5-trisphosphate binding proteinQ62688Rattus norvegicusPredicted (SEA)1.55698
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)5545.2
Click to view 3D structureFarnesyl pyrophosphate synthaseQ0GKD7Leishmania donovaniPredicted (SEA)68.2738
Farnesyl pyrophosphate synthase structureClick to view 3D structureFarnesyl pyrophosphate synthaseP14324HumansPredicted (SEA)436.578
Geranylgeranyl pyrophosphate synthase structureClick to view 3D structureGeranylgeranyl pyrophosphate synthaseO95749HumansPredicted (SEA)149.471
Click to view 3D structurePhosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2Q6P549Mus musculusPredicted (SEA)4.67095
Type II inositol 1,4,5-trisphosphate 5-phosphatase structureClick to view 3D structureType II inositol 1,4,5-trisphosphate 5-phosphataseP32019HumansPredicted (SEA)4.67095
Click to view 3D structureInositol polyphosphate-5-phosphatase AQ14642HumansPredicted (SEA)1.79053
Aminopeptidase N structureClick to view 3D structureAminopeptidase NP04825Escherichia coli (strain K12)Predicted (SEA)21.2528
Click to view 3D structure3-dehydroquinate synthaseP07639Escherichia coli K-12Predicted (SEA)5.99439
Fucose-binding lectin PA-IIL structureClick to view 3D structureFucose-binding lectin PA-IILQ9HYN5Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)Predicted (SEA)19.4623
Autotaxin structureClick to view 3D structureAutotaxinQ13822HumansPredicted (SEA)1999.17
Reverse transcriptase/RNaseH structureClick to view 3D structureReverse transcriptase/RNaseHQ72547Human immunodeficiency virus 1Predicted (SEA)4230.95
Concentrations
Not Available
External Links
DrugBank IDDB00828
HMDB IDHMDB0014966
FooDB IDFDB098105
Phenol Explorer IDNot Available
KNApSAcK IDC00000789
BiGG IDNot Available
BioCyc IDCPD0-1113
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFosfomycin
Chemspider ID394204
ChEBI ID28915
PubChem Compound ID446987
Kegg Compound IDC06454
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=105327
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17124631
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19308743
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2660079
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=288976
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=3464490
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=3900889
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=488578
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=614140
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=6348659
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6796449
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=7030849
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=7224844
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=740308
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=9309262
16. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.
17. Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.