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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-02-26 19:02:32 UTC

Update Date

2023-02-21 17:29:21 UTC

HMDB ID

HMDB0059758

Secondary Accession Numbers

HMDB59758

Metabolite Identification

Common Name

2-Hydroxy-2-ethylsuccinic acid

Description

2-Hydroxy-2-ethylsuccinic acid belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2-Hydroxy-2-ethylsuccinic 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
2-Hydroxy-2-ethylsuccinate	Generator
(R)-2-Ethylmalic acid	Generator
2-Ethylmalic acid	Generator

Chemical Formula

C₆H₁₀O₅

Average Molecular Weight

162.1406

Monoisotopic Molecular Weight

162.05282343

IUPAC Name

2-ethyl-2-hydroxybutanedioic acid

Traditional Name

2-ethyl-2-hydroxybutanedioic acid

CAS Registry Number

Not Available

SMILES

CCC(O)(CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C6H10O5/c1-2-6(11,5(9)10)3-4(7)8/h11H,2-3H2,1H3,(H,7,8)(H,9,10)

InChI Key

YVYGHRNLPUMVBU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Branched fatty acid
Methyl-branched fatty acid
Short-chain hydroxy acid
Hydroxy fatty acid
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Tertiary alcohol
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 2338430)

Source

Exogenous

Exogenous (HMDB: HMDB0059758)

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	284 g/L	ALOGPS
logP	-0.86	ALOGPS
logP	-0.16	ChemAxon
logS	0.24	ALOGPS
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.11 m³·mol⁻¹	ChemAxon
Polarizability	14.49 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]+	136.266	31661259
DarkChem	[M-H]-	132.49	31661259
DeepCCS	[M+H]+	128.107	30932474
DeepCCS	[M-H]-	124.339	30932474
DeepCCS	[M-2H]-	161.594	30932474
DeepCCS	[M+Na]+	136.763	30932474
AllCCS	[M+H]+	137.0	32859911
AllCCS	[M+H-H2O]+	133.0	32859911
AllCCS	[M+NH4]+	140.7	32859911
AllCCS	[M+Na]+	141.7	32859911
AllCCS	[M-H]-	129.4	32859911
AllCCS	[M+Na-2H]-	131.2	32859911
AllCCS	[M+HCOO]-	133.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-2-ethylsuccinic acid	CCC(O)(CC(O)=O)C(O)=O	2388.9	Standard polar	33892256
2-Hydroxy-2-ethylsuccinic acid	CCC(O)(CC(O)=O)C(O)=O	1045.5	Standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid	CCC(O)(CC(O)=O)C(O)=O	1436.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-2-ethylsuccinic acid,1TMS,isomer #1	CCC(CC(=O)O)(O[Si](C)(C)C)C(=O)O	1457.1	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,1TMS,isomer #2	CCC(O)(CC(=O)O[Si](C)(C)C)C(=O)O	1419.7	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,1TMS,isomer #3	CCC(O)(CC(=O)O)C(=O)O[Si](C)(C)C	1379.4	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,2TMS,isomer #1	CCC(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O	1495.4	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,2TMS,isomer #2	CCC(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1486.6	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,2TMS,isomer #3	CCC(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1442.9	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,3TMS,isomer #1	CCC(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1556.3	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,1TBDMS,isomer #1	CCC(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O	1685.1	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,1TBDMS,isomer #2	CCC(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1659.6	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,1TBDMS,isomer #3	CCC(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1653.3	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,2TBDMS,isomer #1	CCC(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O	1945.4	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,2TBDMS,isomer #2	CCC(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1931.7	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,2TBDMS,isomer #3	CCC(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1905.1	Semi standard non polar	33892256
2-Hydroxy-2-ethylsuccinic acid,3TBDMS,isomer #1	CCC(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2198.9	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 - 2-Hydroxy-2-ethylsuccinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4u-9300000000-3b1efd4e6b97c0af7915	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid GC-MS (3 TMS) - 70eV, Positive	splash10-01w0-9263000000-f1b2997f241ca1c41fe4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-2-ethylsuccinic 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 - 2-Hydroxy-2-ethylsuccinic acid 10V, Positive-QTOF	splash10-0002-2900000000-9de9c79218396c80afb5	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid 20V, Positive-QTOF	splash10-0hg2-9600000000-e50dbed47a078176c0bf	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid 40V, Positive-QTOF	splash10-0aba-9200000000-a8215b75541bfebafca9	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid 10V, Negative-QTOF	splash10-02t9-3900000000-19d263f9e1447446bd5d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid 20V, Negative-QTOF	splash10-06dj-9600000000-746d339ab74d06a14184	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid 40V, Negative-QTOF	splash10-0ab9-9000000000-ca45ee65e3a881bf781f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid 10V, Negative-QTOF	splash10-03di-1900000000-d3235bdb7cc86cfb0029	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid 20V, Negative-QTOF	splash10-01ba-9400000000-b4b85b154bf3fe55e37e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid 40V, Negative-QTOF	splash10-052f-9000000000-05764cb2e5e505230cb6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid 10V, Positive-QTOF	splash10-014j-6900000000-5389445ea4aed73b2bc0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid 20V, Positive-QTOF	splash10-00di-9300000000-2217f3a332644db7c277	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2-ethylsuccinic acid 40V, Positive-QTOF	splash10-0a4j-9000000000-ae3a250b45c2b1277563	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	2338430	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

388797

KEGG Compound ID

C02488

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439736

PDB ID

Not Available

ChEBI ID

89897

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

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 2-Hydroxy-2-ethylsuccinic acid (HMDB0059758)

MOL for HMDB0059758 (2-Hydroxy-2-ethylsuccinic acid)

3D MOL for HMDB0059758 (2-Hydroxy-2-ethylsuccinic acid)

3D SDF for HMDB0059758 (2-Hydroxy-2-ethylsuccinic acid)

3D-SDF for HMDB0059758 (2-Hydroxy-2-ethylsuccinic acid)

PDB for HMDB0059758 (2-Hydroxy-2-ethylsuccinic acid)

3D PDB for HMDB0059758 (2-Hydroxy-2-ethylsuccinic acid)

SMILES for HMDB0059758 (2-Hydroxy-2-ethylsuccinic acid)

INCHI for HMDB0059758 (2-Hydroxy-2-ethylsuccinic acid)

Structure for HMDB0059758 (2-Hydroxy-2-ethylsuccinic acid)

3D Structure for HMDB0059758 (2-Hydroxy-2-ethylsuccinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra