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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-09 19:57:04 UTC

Update Date

2023-02-21 17:30:36 UTC

HMDB ID

HMDB0061930

Secondary Accession Numbers

HMDB61930

Metabolite Identification

Common Name

4-Ethoxy-4-oxobutanoic acid

Description

4-Ethoxy-4-oxobutanoic acid belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. 4-Ethoxy-4-oxobutanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

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-oxobutanoate	Generator
Succinic acid monoethyl ester	MeSH
Monoethyl succinate	MeSH
Monoethyl succinic acid	Generator

Chemical Formula

C₆H₁₀O₄

Average Molecular Weight

146.1412

Monoisotopic Molecular Weight

146.057908808

IUPAC Name

4-ethoxy-4-oxobutanoic acid

Traditional Name

4-ethoxy-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

CCOC(=O)CCC(O)=O

InChI Identifier

InChI=1S/C6H10O4/c1-2-10-6(9)4-3-5(7)8/h2-4H2,1H3,(H,7,8)

InChI Key

LOLKAJARZKDJTD-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
Dicarboxylic acid or derivatives
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

Saliva (HMDB: HMDB0061930)

Source

Exogenous

Exogenous (HMDB: HMDB0061930)

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
Water Solubility	72.4 g/L	ALOGPS
logP	0.24	ALOGPS
logP	0.1	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-7	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	5	ChemAxon
Refractivity	33.05 m³·mol⁻¹	ChemAxon
Polarizability	14.2 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
DarkChem	[M+H]+	131.569	31661259
DarkChem	[M-H]-	128.535	31661259
DeepCCS	[M+H]+	126.923	30932474
DeepCCS	[M-H]-	123.877	30932474
DeepCCS	[M-2H]-	160.395	30932474
DeepCCS	[M+Na]+	135.484	30932474
AllCCS	[M+H]+	134.2	32859911
AllCCS	[M+H-H2O]+	130.1	32859911
AllCCS	[M+NH4]+	137.9	32859911
AllCCS	[M+Na]+	139.0	32859911
AllCCS	[M-H]-	131.5	32859911
AllCCS	[M+Na-2H]-	133.8	32859911
AllCCS	[M+HCOO]-	136.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Ethoxy-4-oxobutanoic acid	CCOC(=O)CCC(O)=O	2204.5	Standard polar	33892256
4-Ethoxy-4-oxobutanoic acid	CCOC(=O)CCC(O)=O	1083.9	Standard non polar	33892256
4-Ethoxy-4-oxobutanoic acid	CCOC(=O)CCC(O)=O	1207.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Ethoxy-4-oxobutanoic acid,1TMS,isomer #1	CCOC(=O)CCC(=O)O[Si](C)(C)C	1243.7	Semi standard non polar	33892256
4-Ethoxy-4-oxobutanoic acid,1TBDMS,isomer #1	CCOC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C	1454.1	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-oxobutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fmi-9300000000-05d9494638a198654b26	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethoxy-4-oxobutanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00fs-9800000000-ff70e1642e88c8a79473	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethoxy-4-oxobutanoic 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 - 4-Ethoxy-4-oxobutanoic acid 10V, Positive-QTOF	splash10-0f92-2900000000-57c3059463ba106aa590	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobutanoic acid 20V, Positive-QTOF	splash10-0zfs-9600000000-8cbbcf8a9cd227b9081d	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobutanoic acid 40V, Positive-QTOF	splash10-05di-9000000000-4e5403037abedaffec4f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobutanoic acid 10V, Negative-QTOF	splash10-0002-7900000000-a7a85da5a031b0d46870	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobutanoic acid 20V, Negative-QTOF	splash10-0002-9400000000-8738befe55909bca3c5b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobutanoic acid 40V, Negative-QTOF	splash10-0592-9000000000-503335ecf159ef3323a7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobutanoic acid 10V, Positive-QTOF	splash10-0zmi-9500000000-5035fc110288fd481d7a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobutanoic acid 20V, Positive-QTOF	splash10-0ac3-9100000000-047d4c92982cf9d10bcf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobutanoic acid 40V, Positive-QTOF	splash10-0a4m-9000000000-dbd120b219e7e93913d3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobutanoic acid 10V, Negative-QTOF	splash10-0002-9100000000-85750be4b489e127a601	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobutanoic acid 20V, Negative-QTOF	splash10-0aba-9000000000-ebd1b159039f1952ec2c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethoxy-4-oxobutanoic acid 40V, Negative-QTOF	splash10-0ab9-9000000000-15c649907104ba985ae1	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	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

63778

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70610

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

Venkata Subbaiah B, Sree Ganesh KK, Vamsi Krishna G, Vyas K, Vasu Dev R, Subramanyam Reddy K: Isolation and characterisation of degradant impurities in dipyridamole formulation. J Pharm Biomed Anal. 2012 Mar 5;61:256-64. doi: 10.1016/j.jpba.2011.11.028. Epub 2011 Dec 9. [PubMed:22206889 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 4-Ethoxy-4-oxobutanoic acid (HMDB0061930)

MOL for HMDB0061930 (4-Ethoxy-4-oxobutanoic acid)

3D MOL for HMDB0061930 (4-Ethoxy-4-oxobutanoic acid)

3D SDF for HMDB0061930 (4-Ethoxy-4-oxobutanoic acid)

3D-SDF for HMDB0061930 (4-Ethoxy-4-oxobutanoic acid)

PDB for HMDB0061930 (4-Ethoxy-4-oxobutanoic acid)

3D PDB for HMDB0061930 (4-Ethoxy-4-oxobutanoic acid)

SMILES for HMDB0061930 (4-Ethoxy-4-oxobutanoic acid)

INCHI for HMDB0061930 (4-Ethoxy-4-oxobutanoic acid)

Structure for HMDB0061930 (4-Ethoxy-4-oxobutanoic acid)

3D Structure for HMDB0061930 (4-Ethoxy-4-oxobutanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra