Human Metabolome Database: Showing metabocard for Fosfomycin (HMDB0014966)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2020-02-26 21:40:43 UTC

HMDB ID

HMDB0014966

Secondary Accession Numbers

HMDB14966

Metabolite Identification

Common Name

Fosfomycin

Description

Fosfomycin 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid	ChEBI
(1R,2S)-Epoxypropylphosphonic acid	ChEBI
(2R-cis)-(3-Methyloxiranyl)phosphonic acid	ChEBI
1R-cis-(1,2-Epoxypropyl)phosphonic acid	ChEBI
cis-(1R,2S)-Epoxypropylphosphonic acid	ChEBI
FCM	ChEBI
Fosfomicina	ChEBI
Fosfomycine	ChEBI
Fosfomycinum	ChEBI
L-cis-1,2-Epoxypropylphosphonic acid	ChEBI
Phosphomycin	ChEBI
Phosphonemycin	ChEBI
Phosphonomycin	ChEBI
(1R,2S)-Epoxypropylphosphonate	Kegg
(-)-(1R,2S)-(1,2-Epoxypropyl)phosphonate	Generator
(2R-cis)-(3-Methyloxiranyl)phosphonate	Generator
1R-cis-(1,2-Epoxypropyl)phosphonate	Generator
cis-(1R,2S)-Epoxypropylphosphonate	Generator
L-cis-1,2-Epoxypropylphosphonate	Generator
Fosfocina	HMDB
Fosfomycin disodium salt	HMDB
Fosfomycin sodium	HMDB
Fosfonomycin	HMDB
Phosphomycin disodium salt	HMDB
Fosfomycin tromethamine	HMDB
Fosfomycin trometamol salt	HMDB
Tromethamine, fosfomycin	HMDB
Monuril	HMDB

Chemical Formula

C₃H₇O₄P

Average Molecular Weight

138.059

Monoisotopic Molecular Weight

138.008195224

IUPAC Name

[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid

Traditional Name

fosfomycin

CAS Registry Number

23155-02-4

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 Key

YMDXZJFXQJVXBF-STHAYSLISA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Organic phosphonic acids

Direct Parent

Organic 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

epoxide (CHEBI:28915 )
phosphonic acids (CHEBI:28915 )
Aliphatic compounds (C06454 )

Ontology

Disposition

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Drug

Household products:

Antimicrobial agent:

Antibacterial

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	94 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	46.9 g/L	Not Available
LogP	-1.6	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	46.9 g/L	ALOGPS
logP	-0.86	ALOGPS
logP	-0.74	ChemAxon
logS	-0.47	ALOGPS
pKa (Strongest Acidic)	1.25	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	25.87 m³·mol⁻¹	ChemAxon
Polarizability	10.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-03di-2980000000-005d5b96a1e9219362d0	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-03di-2980000000-005d5b96a1e9219362d0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-9100000000-f3dc2512a6ad53fb9238	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1900000000-3025442157ee47184674	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-275a01dd7f8cc74a7b6f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-859fa61894a0825e23d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3900000000-22234a977a4d3da18ecf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05qi-9500000000-81b95429a7694bba36c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-9000000000-d2dbdb85a43ce508ab14	Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00828	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00828	21059682	details