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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:40:00 UTC
HMDB IDHMDB0014966
Secondary Accession Numbers
  • HMDB14966
Metabolite Identification
Common NameFosfomycin
DescriptionFosfomycin, also known as phosphonomycin or FCM, belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid. Fosfomycin has been detected, but not quantified in, milk (cow). This could make fosfomycin a potential biomarker for the consumption of these foods. Fosfomycin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Fosfomycin.
Structure
Data?1582753243
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 Weight138.059
Monoisotopic Molecular Weight138.008195224
IUPAC Name[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
Traditional Namefosfomycin
CAS Registry Number23155-02-4
SMILES
[H][C@@]1(C)O[C@]1([H])P(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
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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point94 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility46.9 g/LNot Available
LogP-1.6Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility46.9 g/LALOGPS
logP10(-0.86) g/LALOGPS
logP10(-0.74) g/LChemAxon
logS10(-0.47) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.71331661259
DarkChem[M-H]-123.77831661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Fosfomycin GC-MS (2 TMS)splash10-03di-2980000000-005d5b96a1e9219362d02014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fosfomycin GC-MS (Non-derivatized)splash10-03di-2980000000-005d5b96a1e9219362d02017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosfomycin GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-9100000000-f3dc2512a6ad53fb92382017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosfomycin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosfomycin 10V, Positive-QTOFsplash10-000i-1900000000-3025442157ee471846742016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosfomycin 20V, Positive-QTOFsplash10-001i-9100000000-275a01dd7f8cc74a7b6f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosfomycin 40V, Positive-QTOFsplash10-001i-9100000000-859fa61894a0825e23d22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosfomycin 10V, Negative-QTOFsplash10-000i-3900000000-22234a977a4d3da18ecf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosfomycin 20V, Negative-QTOFsplash10-05qi-9500000000-81b95429a7694bba36c72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosfomycin 40V, Negative-QTOFsplash10-057i-9000000000-d2dbdb85a43ce508ab142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosfomycin 10V, Positive-QTOFsplash10-000i-2900000000-3865d3126791b7f8f8f32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosfomycin 20V, Positive-QTOFsplash10-000b-9400000000-d43f705d0ad2bb7e25c92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosfomycin 40V, Positive-QTOFsplash10-06tn-9000000000-5460c55de4fe7bea9b0d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosfomycin 10V, Negative-QTOFsplash10-03dr-9400000000-f59b9b60406eacd3c3da2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosfomycin 20V, Negative-QTOFsplash10-03fr-9000000000-eb71c23b854ab0f65f4a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosfomycin 40V, Negative-QTOFsplash10-03di-9000000000-987956f210941d36e4582021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00828 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00828 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00828
Phenol Explorer Compound IDNot Available
FooDB IDFDB098105
KNApSAcK IDC00000789
Chemspider ID394204
KEGG Compound IDC06454
BioCyc IDCPD0-1113
BiGG IDNot Available
Wikipedia LinkFosfomycin
METLIN IDNot Available
PubChem Compound446987
PDB IDNot Available
ChEBI ID28915
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available