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Record Information
Version4.0
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-09-27 08:27:46 UTC
HMDB IDHMDB0014966
Secondary Accession Numbers
  • HMDB14966
Metabolite Identification
Common NameFosfomycin
DescriptionFosfomycin is only found in individuals that have used or taken this drug. It is an antibiotic produced by Streptomyces fradiae. [PubChem]Fosfomycin is a phosphoenolpyruvate analogue produced by Streptomyces that irreversibly inhibits enolpyruvate transferase (MurA), which prevents the formation of N-acetylmuramic acid, an essential element of the peptidoglycan cell wall.
Structure
Thumb
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)-(1,2-Epoxypropyl)phosphonateGenerator
(1R,2S)-EpoxypropylphosphonateGenerator
(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 tromethamineMeSH
Fosfomycin trometamol saltMeSH
Tromethamine, fosfomycinMeSH
MonurilMeSH
Chemical FormulaC3H7O4P
Average Molecular Weight138.059
Monoisotopic Molecular Weight138.008195224
IUPAC Name[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
Traditional Namefosfomycin
CAS Registry Number23155-02-4
SMILES
C[C@@H]1O[C@@H]1P(O)(O)=O
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of chemical entities known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassOrganic phosphonic acids and derivatives
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

    Antimicrobial agent:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point94 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility46.9 g/LNot Available
LogP-1.6Not 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03di-2980000000-005d5b96a1e9219362d0View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-03di-2980000000-005d5b96a1e9219362d0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900000000-3025442157ee47184674View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-275a01dd7f8cc74a7b6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9100000000-859fa61894a0825e23d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3900000000-22234a977a4d3da18ecfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05qi-9500000000-81b95429a7694bba36c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-9000000000-d2dbdb85a43ce508ab14View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00828 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00828 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00828
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID394204
KEGG Compound IDC06454
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFosfomycin
METLIN IDNot Available
PubChem Compound446987
PDB IDFCN
ChEBI ID28915
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available