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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2023-02-21 17:18:20 UTC

HMDB ID

HMDB0014966

Secondary Accession Numbers

HMDB14966

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 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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

Not Available

Not Available

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.713	31661259
DarkChem	[M-H]-	123.778	31661259
DeepCCS	[M+H]+	123.735	30932474
DeepCCS	[M-H]-	121.627	30932474
DeepCCS	[M-2H]-	156.23	30932474
DeepCCS	[M+Na]+	130.328	30932474
AllCCS	[M+H]+	131.5	32859911
AllCCS	[M+H-H2O]+	127.1	32859911
AllCCS	[M+NH4]+	135.6	32859911
AllCCS	[M+Na]+	136.8	32859911
AllCCS	[M-H]-	123.6	32859911
AllCCS	[M+Na-2H]-	126.3	32859911
AllCCS	[M+HCOO]-	129.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.93 minutes	32390414
Predicted by Siyang on May 30, 2022	9.4074 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.51 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	276.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	790.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	362.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	72.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	235.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	54.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	291.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	307.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	375.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	644.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	86.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	782.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	598.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	362.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	333.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fosfomycin	[H][C@@]1(C)O[C@]1([H])P(O)(O)=O	2126.0	Standard polar	33892256
Fosfomycin	[H][C@@]1(C)O[C@]1([H])P(O)(O)=O	1171.0	Standard non polar	33892256
Fosfomycin	[H][C@@]1(C)O[C@]1([H])P(O)(O)=O	1220.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fosfomycin,1TMS,isomer #1	C[C@@H]1O[C@@H]1P(=O)(O)O[Si](C)(C)C	1232.9	Semi standard non polar	33892256
Fosfomycin,1TMS,isomer #1	C[C@@H]1O[C@@H]1P(=O)(O)O[Si](C)(C)C	1166.3	Standard non polar	33892256
Fosfomycin,1TMS,isomer #1	C[C@@H]1O[C@@H]1P(=O)(O)O[Si](C)(C)C	1499.5	Standard polar	33892256
Fosfomycin,2TMS,isomer #1	C[C@@H]1O[C@@H]1P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1275.8	Semi standard non polar	33892256
Fosfomycin,2TMS,isomer #1	C[C@@H]1O[C@@H]1P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1323.3	Standard non polar	33892256
Fosfomycin,2TMS,isomer #1	C[C@@H]1O[C@@H]1P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1355.3	Standard polar	33892256
Fosfomycin,1TBDMS,isomer #1	C[C@@H]1O[C@@H]1P(=O)(O)O[Si](C)(C)C(C)(C)C	1482.0	Semi standard non polar	33892256
Fosfomycin,1TBDMS,isomer #1	C[C@@H]1O[C@@H]1P(=O)(O)O[Si](C)(C)C(C)(C)C	1412.9	Standard non polar	33892256
Fosfomycin,1TBDMS,isomer #1	C[C@@H]1O[C@@H]1P(=O)(O)O[Si](C)(C)C(C)(C)C	1668.8	Standard polar	33892256
Fosfomycin,2TBDMS,isomer #1	C[C@@H]1O[C@@H]1P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1733.7	Semi standard non polar	33892256
Fosfomycin,2TBDMS,isomer #1	C[C@@H]1O[C@@H]1P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1775.4	Standard non polar	33892256
Fosfomycin,2TBDMS,isomer #1	C[C@@H]1O[C@@H]1P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1663.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Fosfomycin GC-MS (2 TMS)	splash10-03di-2980000000-005d5b96a1e9219362d0	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Fosfomycin GC-MS (Non-derivatized)	splash10-03di-2980000000-005d5b96a1e9219362d0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fosfomycin GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-9100000000-f3dc2512a6ad53fb9238	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fosfomycin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosfomycin 10V, Positive-QTOF	splash10-000i-1900000000-3025442157ee47184674	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosfomycin 20V, Positive-QTOF	splash10-001i-9100000000-275a01dd7f8cc74a7b6f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosfomycin 40V, Positive-QTOF	splash10-001i-9100000000-859fa61894a0825e23d2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosfomycin 10V, Negative-QTOF	splash10-000i-3900000000-22234a977a4d3da18ecf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosfomycin 20V, Negative-QTOF	splash10-05qi-9500000000-81b95429a7694bba36c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosfomycin 40V, Negative-QTOF	splash10-057i-9000000000-d2dbdb85a43ce508ab14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosfomycin 10V, Positive-QTOF	splash10-000i-2900000000-3865d3126791b7f8f8f3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosfomycin 20V, Positive-QTOF	splash10-000b-9400000000-d43f705d0ad2bb7e25c9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosfomycin 40V, Positive-QTOF	splash10-06tn-9000000000-5460c55de4fe7bea9b0d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosfomycin 10V, Negative-QTOF	splash10-03dr-9400000000-f59b9b60406eacd3c3da	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosfomycin 20V, Negative-QTOF	splash10-03fr-9000000000-eb71c23b854ab0f65f4a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosfomycin 40V, Negative-QTOF	splash10-03di-9000000000-987956f210941d36e458	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00828

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Fosfomycin (HMDB0014966)

MOL for HMDB0014966 (Fosfomycin)

3D MOL for HMDB0014966 (Fosfomycin)

3D SDF for HMDB0014966 (Fosfomycin)

3D-SDF for HMDB0014966 (Fosfomycin)

PDB for HMDB0014966 (Fosfomycin)

3D PDB for HMDB0014966 (Fosfomycin)

SMILES for HMDB0014966 (Fosfomycin)

INCHI for HMDB0014966 (Fosfomycin)

Structure for HMDB0014966 (Fosfomycin)

3D Structure for HMDB0014966 (Fosfomycin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra