Showing metabocard for Fosfomycin (BMDB0062043)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-06-25 21:46:16 UTC
Update Date2020-05-05 18:40:38 UTC
BMDB IDBMDB0062043
Secondary Accession Numbers
  • BMDB62043
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 is a drug which is used for the treatment of uncomplicated urinary tract infections (acute cystitis) in women due to susceptible strains of escherichia coli and enterococcus faecalis. Fosfomycin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
StatusDetected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 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-MS (Non-derivatized)splash10-03di-2980000000-005d5b96a1e9219362d0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-9100000000-f3dc2512a6ad53fb9238View 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-3865d3126791b7f8f8f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-9400000000-d43f705d0ad2bb7e25c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06tn-9000000000-5460c55de4fe7bea9b0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dr-9400000000-f59b9b60406eacd3c3daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-9000000000-eb71c23b854ab0f65f4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9000000000-987956f210941d36e458View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Mammary Gland
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
HMDB IDHMDB0014966
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:23438684 ]
  2. 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. [PubMed:25599412 ]