You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:30:48 UTC
HMDB IDHMDB14966
Secondary Accession NumbersNone
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
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 KeyInChIKey=YMDXZJFXQJVXBF-STHAYSLISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganic phosphonic acids and derivatives
Sub ClassOrganic phosphonic acids
Direct ParentOrganic phosphonic acids
Alternative Parents
Substituents
  • Organophosphonic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Oxirane
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Bacterial Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point94 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.69e+01 g/LNot Available
LogP-1.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility46.9 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.87 m3·mol-1ChemAxon
Polarizability10.8 Å3ChemAxon
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00828
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00828
  • Not Applicable
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
NuGOwiki LinkHMDB14966
Metagene LinkHMDB14966
METLIN IDNot Available
PubChem Compound446987
PDB IDFCN
ChEBI ID28915
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available