Milk Composition Database: Showing metabocard for Fosfomycin (BMDB0062043)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2018-06-25 21:46:16 UTC

Update Date

2020-05-05 18:40:38 UTC

MCDB ID

BMDB0062043

Secondary Accession Numbers

BMDB62043

Metabolite Identification

Common Name

Fosfomycin

Description

Fosfomycin, 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	1	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	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-03di-2980000000-005d5b96a1e9219362d0	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-03di-2980000000-005d5b96a1e9219362d0	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-9100000000-f3dc2512a6ad53fb9238	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1900000000-3025442157ee47184674	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-275a01dd7f8cc74a7b6f	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-859fa61894a0825e23d2	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3900000000-22234a977a4d3da18ecf	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05qi-9500000000-81b95429a7694bba36c7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-9000000000-d2dbdb85a43ce508ab14	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-3865d3126791b7f8f8f3	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000b-9400000000-d43f705d0ad2bb7e25c9	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06tn-9000000000-5460c55de4fe7bea9b0d	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dr-9400000000-f59b9b60406eacd3c3da	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fr-9000000000-eb71c23b854ab0f65f4a	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9000000000-987956f210941d36e458	2021-10-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 23438684	details
Detected but not Quantified	Not Applicable		PMID: 25599412	details

External Links

HMDB ID

HMDB0014966

DrugBank ID

DB00828

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Fosfomycin

METLIN ID

Not Available

PubChem Compound

446987

PDB ID

Not Available

ChEBI ID

28915

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]

Showing metabocard for Fosfomycin (BMDB0062043)

Structure for BMDB0062043 (Fosfomycin)