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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:26:17 UTC

Update Date

2021-09-26 22:55:29 UTC

HMDB ID

HMDB0246416

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Ethoxy-4-oxobut-2-enoic acid

Description

4-ethoxy-4-oxobut-2-enoic acid belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a significant number of articles have been published on 4-ethoxy-4-oxobut-2-enoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-ethoxy-4-oxobut-2-enoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Ethoxy-4-oxobut-2-enoic 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
4-Ethoxy-4-oxobut-2-enoate	Generator
Diethyl maleic acid diester	MeSH
Ethyl maleate	MeSH
Diethyl maleate	MeSH
Diethylmaleate	MeSH
Monoethyl maleate	MeSH
Maleic acid diethyl ester	MeSH
Maleic acid, ethyl ester	MeSH
Ethyl hydrogen maleate	MeSH

Chemical Formula

C₆H₈O₄

Average Molecular Weight

144.126

Monoisotopic Molecular Weight

144.042258738

IUPAC Name

4-ethoxy-4-oxobut-2-enoic acid

Traditional Name

4-ethoxy-4-oxobut-2-enoic acid

CAS Registry Number

Not Available

SMILES

CCOC(=O)C=CC(O)=O

InChI Identifier

InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)

InChI Key

XLYMOEINVGRTEX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	0.86	ALOGPS
logP	0.7	ChemAxon
logS	-0.76	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.12 m³·mol⁻¹	ChemAxon
Polarizability	13.57 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]+	126.884	30932474
DeepCCS	[M-H]-	123.757	30932474
DeepCCS	[M-2H]-	160.302	30932474
DeepCCS	[M+Na]+	135.443	30932474
AllCCS	[M+H]+	132.9	32859911
AllCCS	[M+H-H2O]+	128.8	32859911
AllCCS	[M+NH4]+	136.7	32859911
AllCCS	[M+Na]+	137.8	32859911
AllCCS	[M-H]-	129.6	32859911
AllCCS	[M+Na-2H]-	131.9	32859911
AllCCS	[M+HCOO]-	134.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Ethoxy-4-oxobut-2-enoic acid	CCOC(=O)C=CC(O)=O	2319.7	Standard polar	33892256
4-Ethoxy-4-oxobut-2-enoic acid	CCOC(=O)C=CC(O)=O	1205.9	Standard non polar	33892256
4-Ethoxy-4-oxobut-2-enoic acid	CCOC(=O)C=CC(O)=O	1257.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0092-9000000000-eb17e7385d8add87de15	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 30V, Negative-QTOF	splash10-00di-9000000000-9f13687edb7af47430fd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 15V, Negative-QTOF	splash10-00di-9000000000-1eeef651b9a53276ccd7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 45V, Negative-QTOF	splash10-00di-9000000000-3c2a0b44de43b3ce4324	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 60V, Negative-QTOF	splash10-00di-9000000000-c967b31017727ef06409	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 75V, Positive-QTOF	splash10-00di-9000000000-b27545aa7fbc501e8f0b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 75V, Negative-QTOF	splash10-00di-9000000000-0d8f5a3861ff419425fc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 90V, Negative-QTOF	splash10-00di-9000000000-b548ad7f97f1fe3bc3c5	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 10V, Positive-QTOF	splash10-0002-5900000000-e1b9153a7186f86056ca	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 20V, Positive-QTOF	splash10-0002-9200000000-af4023c01d62236cde37	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 40V, Positive-QTOF	splash10-05i1-9000000000-6e9fac19f8c3afd1e8b9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 10V, Negative-QTOF	splash10-0007-9800000000-fa4964b91167a92ec7e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 20V, Negative-QTOF	splash10-0002-9300000000-cadeab4832eafce97db0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 40V, Negative-QTOF	splash10-0f6t-9000000000-bfb0233fab1dae143655	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 10V, Positive-QTOF	splash10-000t-9100000000-093702f284ef987fe3e8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 20V, Positive-QTOF	splash10-0aba-9000000000-987adc5d33d18745c5a8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 40V, Positive-QTOF	splash10-052f-9000000000-bd3aafd589c3414a6733	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 10V, Negative-QTOF	splash10-0002-9100000000-8597f839d7c649e71a0a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 20V, Negative-QTOF	splash10-0gi1-9000000000-d576ba5f59716220347c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobut-2-enoic acid 40V, Negative-QTOF	splash10-00xs-9000000000-06a99448184870f7a5b0	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)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

37714

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

41331

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 4-Ethoxy-4-oxobut-2-enoic acid (HMDB0246416)

MOL for HMDB0246416 (4-Ethoxy-4-oxobut-2-enoic acid)

3D MOL for HMDB0246416 (4-Ethoxy-4-oxobut-2-enoic acid)

3D SDF for HMDB0246416 (4-Ethoxy-4-oxobut-2-enoic acid)

3D-SDF for HMDB0246416 (4-Ethoxy-4-oxobut-2-enoic acid)

PDB for HMDB0246416 (4-Ethoxy-4-oxobut-2-enoic acid)

3D PDB for HMDB0246416 (4-Ethoxy-4-oxobut-2-enoic acid)

SMILES for HMDB0246416 (4-Ethoxy-4-oxobut-2-enoic acid)

INCHI for HMDB0246416 (4-Ethoxy-4-oxobut-2-enoic acid)

Structure for HMDB0246416 (4-Ethoxy-4-oxobut-2-enoic acid)

3D Structure for HMDB0246416 (4-Ethoxy-4-oxobut-2-enoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra