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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-01 18:18:59 UTC

Update Date

2021-09-26 22:48:59 UTC

HMDB ID

HMDB0242559

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2S,3R)-3-Methyloxiran-2-ylphosphonic acid

Description

(3-methyloxiran-2-yl)phosphonic acid belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid. Based on a literature review very few articles have been published on (3-methyloxiran-2-yl)phosphonic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2s,3r)-3-methyloxiran-2-ylphosphonic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2S,3R)-3-Methyloxiran-2-ylphosphonic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3-Methyloxiran-2-yl)phosphonate	Generator
1,2-EPOXYPROPYLPHOSPHONate	Generator, HMDB
Fosfomycin	MeSH, HMDB
Monuril	MeSH, HMDB
Phosphonomycin	MeSH, HMDB
Fosfomycin tromethamine	MeSH, HMDB
Fosfomycin trometamol salt	MeSH, HMDB
Phosphomycin	MeSH, HMDB
Tromethamine, fosfomycin	MeSH, HMDB
(2S,3R)-3-Methyloxiran-2-ylphosphonate	Generator

Chemical Formula

C₃H₇O₄P

Average Molecular Weight

138.059

Monoisotopic Molecular Weight

138.008195703

IUPAC Name

(3-methyloxiran-2-yl)phosphonic acid

Traditional Name

fosfomycin calcium

CAS Registry Number

Not Available

SMILES

CC1OC1P(O)(O)=O

InChI Identifier

InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)

InChI Key

YMDXZJFXQJVXBF-UHFFFAOYSA-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	10.82 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
DeepCCS	[M+H]+	124.348	30932474
DeepCCS	[M-H]-	121.548	30932474
DeepCCS	[M-2H]-	157.992	30932474
DeepCCS	[M+Na]+	132.636	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 Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2S,3R)-3-Methyloxiran-2-ylphosphonic acid,1TMS,isomer #1	CC1OC1P(=O)(O)O[Si](C)(C)C	1255.8	Semi standard non polar	33892256
(2S,3R)-3-Methyloxiran-2-ylphosphonic acid,1TMS,isomer #1	CC1OC1P(=O)(O)O[Si](C)(C)C	1184.1	Standard non polar	33892256
(2S,3R)-3-Methyloxiran-2-ylphosphonic acid,1TMS,isomer #1	CC1OC1P(=O)(O)O[Si](C)(C)C	1565.7	Standard polar	33892256
(2S,3R)-3-Methyloxiran-2-ylphosphonic acid,2TMS,isomer #1	CC1OC1P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1290.5	Semi standard non polar	33892256
(2S,3R)-3-Methyloxiran-2-ylphosphonic acid,2TMS,isomer #1	CC1OC1P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1326.0	Standard non polar	33892256
(2S,3R)-3-Methyloxiran-2-ylphosphonic acid,2TMS,isomer #1	CC1OC1P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1353.6	Standard polar	33892256
(2S,3R)-3-Methyloxiran-2-ylphosphonic acid,1TBDMS,isomer #1	CC1OC1P(=O)(O)O[Si](C)(C)C(C)(C)C	1515.4	Semi standard non polar	33892256
(2S,3R)-3-Methyloxiran-2-ylphosphonic acid,1TBDMS,isomer #1	CC1OC1P(=O)(O)O[Si](C)(C)C(C)(C)C	1420.6	Standard non polar	33892256
(2S,3R)-3-Methyloxiran-2-ylphosphonic acid,1TBDMS,isomer #1	CC1OC1P(=O)(O)O[Si](C)(C)C(C)(C)C	1726.2	Standard polar	33892256
(2S,3R)-3-Methyloxiran-2-ylphosphonic acid,2TBDMS,isomer #1	CC1OC1P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1736.0	Semi standard non polar	33892256
(2S,3R)-3-Methyloxiran-2-ylphosphonic acid,2TBDMS,isomer #1	CC1OC1P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1767.9	Standard non polar	33892256
(2S,3R)-3-Methyloxiran-2-ylphosphonic acid,2TBDMS,isomer #1	CC1OC1P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1654.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3R)-3-Methyloxiran-2-ylphosphonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-9100000000-f3dc2512a6ad53fb9238	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3R)-3-Methyloxiran-2-ylphosphonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,3R)-3-Methyloxiran-2-ylphosphonic acid 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 - (2S,3R)-3-Methyloxiran-2-ylphosphonic acid 10V, Negative-QTOF	splash10-03dr-9400000000-f59b9b60406eacd3c3da	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Methyloxiran-2-ylphosphonic acid 20V, Negative-QTOF	splash10-03fr-9000000000-d51dfe0c614cfc27879b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Methyloxiran-2-ylphosphonic acid 40V, Negative-QTOF	splash10-03di-9000000000-987956f210941d36e458	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Methyloxiran-2-ylphosphonic acid 10V, Positive-QTOF	splash10-000i-2900000000-3865d3126791b7f8f8f3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Methyloxiran-2-ylphosphonic acid 20V, Positive-QTOF	splash10-000b-9400000000-f2c221e48605f3f0f929	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Methyloxiran-2-ylphosphonic acid 40V, Positive-QTOF	splash10-06vv-9000000000-2d7b240b3fd909536b0b	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3299

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3417

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (2S,3R)-3-Methyloxiran-2-ylphosphonic acid (HMDB0242559)

MOL for HMDB0242559 ((2S,3R)-3-Methyloxiran-2-ylphosphonic acid)

3D MOL for HMDB0242559 ((2S,3R)-3-Methyloxiran-2-ylphosphonic acid)

3D SDF for HMDB0242559 ((2S,3R)-3-Methyloxiran-2-ylphosphonic acid)

3D-SDF for HMDB0242559 ((2S,3R)-3-Methyloxiran-2-ylphosphonic acid)

PDB for HMDB0242559 ((2S,3R)-3-Methyloxiran-2-ylphosphonic acid)

3D PDB for HMDB0242559 ((2S,3R)-3-Methyloxiran-2-ylphosphonic acid)

SMILES for HMDB0242559 ((2S,3R)-3-Methyloxiran-2-ylphosphonic acid)

INCHI for HMDB0242559 ((2S,3R)-3-Methyloxiran-2-ylphosphonic acid)

Structure for HMDB0242559 ((2S,3R)-3-Methyloxiran-2-ylphosphonic acid)

3D Structure for HMDB0242559 ((2S,3R)-3-Methyloxiran-2-ylphosphonic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra