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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:58:30 UTC

Update Date

2021-10-01 22:52:03 UTC

HMDB ID

HMDB0256485

Secondary Accession Numbers

None

Metabolite Identification

Common Name

phosphonoacetaldehyde

Description

Phosphonoacetaldehyde, also known as 2-oxoethylphosphonate, belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid. Phosphonoacetaldehyde exists in all living organisms, ranging from bacteria to humans. Phosphonoacetaldehyde 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 Phosphonoacetaldehyde. This compound has been identified in human blood as reported by (PMID: 31557052 ). Phosphonoacetaldehyde is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically phosphonoacetaldehyde 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
2-Oxoethylphosphonate	ChEBI
2-Phosphonoacetaldehyde	ChEBI
2-Oxoethylphosphonic acid	Generator
Acetylphosphonate	MeSH

Chemical Formula

C₂H₅O₄P

Average Molecular Weight

124.0325

Monoisotopic Molecular Weight

123.99254516

IUPAC Name

(2-oxoethyl)phosphonic acid

Traditional Name

phosphonoacetaldehyde

CAS Registry Number

Not Available

SMILES

OP(O)(=O)CC=O

InChI Identifier

InChI=1S/C2H5O4P/c3-1-2-7(4,5)6/h1H,2H2,(H2,4,5,6)

InChI Key

YEMKIGUKNDOZEG-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
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organophosphorus compound
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphonic acids (CHEBI:18124 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	-1.1	ALOGPS
logP	-1.9	ChemAxon
logS	-0.73	ALOGPS
pKa (Strongest Acidic)	1.69	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	22.71 m³·mol⁻¹	ChemAxon
Polarizability	8.75 Å³	ChemAxon
Number of Rings	0	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]+	119.775	30932474
DeepCCS	[M-H]-	116.942	30932474
DeepCCS	[M-2H]-	153.514	30932474
DeepCCS	[M+Na]+	128.078	30932474
AllCCS	[M+H]+	129.3	32859911
AllCCS	[M+H-H2O]+	125.2	32859911
AllCCS	[M+NH4]+	133.2	32859911
AllCCS	[M+Na]+	134.3	32859911
AllCCS	[M-H]-	124.8	32859911
AllCCS	[M+Na-2H]-	128.7	32859911
AllCCS	[M+HCOO]-	133.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
phosphonoacetaldehyde	OP(O)(=O)CC=O	2314.3	Standard polar	33892256
phosphonoacetaldehyde	OP(O)(=O)CC=O	1075.1	Standard non polar	33892256
phosphonoacetaldehyde	OP(O)(=O)CC=O	1197.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
phosphonoacetaldehyde,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)CC=O	1346.0	Semi standard non polar	33892256
phosphonoacetaldehyde,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)CC=O	1225.1	Standard non polar	33892256
phosphonoacetaldehyde,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)CC=O	1794.0	Standard polar	33892256
phosphonoacetaldehyde,1TMS,isomer #2	C[Si](C)(C)OC=CP(=O)(O)O	1374.7	Semi standard non polar	33892256
phosphonoacetaldehyde,1TMS,isomer #2	C[Si](C)(C)OC=CP(=O)(O)O	1380.6	Standard non polar	33892256
phosphonoacetaldehyde,1TMS,isomer #2	C[Si](C)(C)OC=CP(=O)(O)O	1964.9	Standard polar	33892256
phosphonoacetaldehyde,2TMS,isomer #1	C[Si](C)(C)OP(=O)(CC=O)O[Si](C)(C)C	1398.1	Semi standard non polar	33892256
phosphonoacetaldehyde,2TMS,isomer #1	C[Si](C)(C)OP(=O)(CC=O)O[Si](C)(C)C	1343.4	Standard non polar	33892256
phosphonoacetaldehyde,2TMS,isomer #1	C[Si](C)(C)OP(=O)(CC=O)O[Si](C)(C)C	1400.4	Standard polar	33892256
phosphonoacetaldehyde,2TMS,isomer #2	C[Si](C)(C)OC=CP(=O)(O)O[Si](C)(C)C	1441.7	Semi standard non polar	33892256
phosphonoacetaldehyde,2TMS,isomer #2	C[Si](C)(C)OC=CP(=O)(O)O[Si](C)(C)C	1403.8	Standard non polar	33892256
phosphonoacetaldehyde,2TMS,isomer #2	C[Si](C)(C)OC=CP(=O)(O)O[Si](C)(C)C	1614.6	Standard polar	33892256
phosphonoacetaldehyde,3TMS,isomer #1	C[Si](C)(C)OC=CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1475.1	Semi standard non polar	33892256
phosphonoacetaldehyde,3TMS,isomer #1	C[Si](C)(C)OC=CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1464.2	Standard non polar	33892256
phosphonoacetaldehyde,3TMS,isomer #1	C[Si](C)(C)OC=CP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1447.0	Standard polar	33892256
phosphonoacetaldehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)CC=O	1606.6	Semi standard non polar	33892256
phosphonoacetaldehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)CC=O	1468.8	Standard non polar	33892256
phosphonoacetaldehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)CC=O	1926.5	Standard polar	33892256
phosphonoacetaldehyde,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=CP(=O)(O)O	1628.6	Semi standard non polar	33892256
phosphonoacetaldehyde,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=CP(=O)(O)O	1586.8	Standard non polar	33892256
phosphonoacetaldehyde,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=CP(=O)(O)O	2113.2	Standard polar	33892256
phosphonoacetaldehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(CC=O)O[Si](C)(C)C(C)(C)C	1844.9	Semi standard non polar	33892256
phosphonoacetaldehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(CC=O)O[Si](C)(C)C(C)(C)C	1768.5	Standard non polar	33892256
phosphonoacetaldehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(CC=O)O[Si](C)(C)C(C)(C)C	1677.2	Standard polar	33892256
phosphonoacetaldehyde,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=CP(=O)(O)O[Si](C)(C)C(C)(C)C	1888.8	Semi standard non polar	33892256
phosphonoacetaldehyde,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=CP(=O)(O)O[Si](C)(C)C(C)(C)C	1832.3	Standard non polar	33892256
phosphonoacetaldehyde,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=CP(=O)(O)O[Si](C)(C)C(C)(C)C	1877.0	Standard polar	33892256
phosphonoacetaldehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2084.2	Semi standard non polar	33892256
phosphonoacetaldehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2059.7	Standard non polar	33892256
phosphonoacetaldehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1802.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - phosphonoacetaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-0089-9400000000-94bb02803b93b2d7a4ca	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - phosphonoacetaldehyde 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 - phosphonoacetaldehyde 10V, Positive-QTOF	splash10-004i-1900000000-ce5f1d31b9e1260d2ae6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - phosphonoacetaldehyde 20V, Positive-QTOF	splash10-0037-9300000000-1cf50dd723b4390d6a9f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - phosphonoacetaldehyde 40V, Positive-QTOF	splash10-053r-9200000000-ae3f78ad353e2ce27ac4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - phosphonoacetaldehyde 10V, Negative-QTOF	splash10-00di-2900000000-49883056142c18647f43	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - phosphonoacetaldehyde 20V, Negative-QTOF	splash10-0uk9-5900000000-06ca1379a75e573efdd1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - phosphonoacetaldehyde 40V, Negative-QTOF	splash10-002f-9200000000-67f1e5ae5f118e542243	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	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

DB03174

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00000799

Chemspider ID

476

KEGG Compound ID

C03167

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18124

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 ]

Enzymes

Enzyme Details

1. Bifunctional phosphonoacetaldehyde hydrolase/aminoethylphosphonate transaminase

General function:: Not Available
Specific function:: Involved in phosphonate degradation.
Gene Name:: PHNXW
Uniprot ID:: Q183T0
Molecular weight:: 72043.095

Enzyme Details

2. Phosphonoacetaldehyde hydrolase

General function:: Not Available
Specific function:: Involved in phosphonate degradation.
Gene Name:: PHNX
Uniprot ID:: Q5PFR1
Molecular weight:: 28534.35

Enzyme Details

3. 2-aminoethylphosphonate--pyruvate transaminase

General function:: Not Available
Specific function:: Involved in phosphonate degradation.
Gene Name:: PHNW
Uniprot ID:: A6L4N0
Molecular weight:: 40763.395

Enzyme Details

4. 2-aminoethylphosphonate--pyruvate transaminase

General function:: Not Available
Specific function:: Involved in phosphonate degradation.
Gene Name:: PHNW
Uniprot ID:: Q5PFR0
Molecular weight:: 40295.59

Enzyme Details

5. Phosphonoacetaldehyde hydrolase

General function:: Not Available
Specific function:: Involved in phosphonate degradation.
Gene Name:: PHNX
Uniprot ID:: A6LFV1
Molecular weight:: 29556.865

Showing metabocard for phosphonoacetaldehyde (HMDB0256485)

MOL for HMDB0256485 (phosphonoacetaldehyde)

3D MOL for HMDB0256485 (phosphonoacetaldehyde)

3D SDF for HMDB0256485 (phosphonoacetaldehyde)

3D-SDF for HMDB0256485 (phosphonoacetaldehyde)

PDB for HMDB0256485 (phosphonoacetaldehyde)

3D PDB for HMDB0256485 (phosphonoacetaldehyde)

SMILES for HMDB0256485 (phosphonoacetaldehyde)

INCHI for HMDB0256485 (phosphonoacetaldehyde)

Structure for HMDB0256485 (phosphonoacetaldehyde)

3D Structure for HMDB0256485 (phosphonoacetaldehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes