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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:50 UTC

Update Date

2023-02-21 17:21:50 UTC

HMDB ID

HMDB0032269

Secondary Accession Numbers

HMDB32269

Metabolite Identification

Common Name

(+/-)-Ethyl 2-hydroxy-2-methylbutyrate

Description

(+/-)-Ethyl 2-hydroxy-2-methylbutyrate 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 small amount of articles have been published on (+/-)-Ethyl 2-hydroxy-2-methylbutyrate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+/-)-ethyl 2-hydroxy-2-methylbutyric acid	Generator
Butanoic acid, 2-hydroxy-2-methyl-, ethyl ester	HMDB
Ethyl 2-hydroxy-2-methylbutanoate	HMDB
Ethyl 2-hydroxy-2-methylbutyrate	HMDB

Chemical Formula

C₇H₁₄O₃

Average Molecular Weight

146.1843

Monoisotopic Molecular Weight

146.094294314

IUPAC Name

ethyl 2-hydroxy-2-methylbutanoate

Traditional Name

ethyl 2-hydroxy-2-methylbutanoate

CAS Registry Number

77-70-3

SMILES

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

InChI Identifier

InChI=1S/C7H14O3/c1-4-7(3,9)6(8)10-5-2/h9H,4-5H2,1-3H3

InChI Key

KIYWRWLZHQZKKD-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
Tertiary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0032269)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032269)

Source

Endogenous

Endogenous (HMDB: HMDB0032269)

Animal

Animal (HMDB: HMDB0032269)

Exogenous

Food

Food (HMDB: HMDB0032269)

Exogenous (HMDB: HMDB0032269)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032269)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032269)

Lipid metabolism pathway (HMDB: HMDB0032269)

Cellular process

Cell signaling (HMDB: HMDB0032269)

Biochemical process

Lipid transport (HMDB: HMDB0032269)

Role

Biological role

Energy source (HMDB: HMDB0032269)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032269)

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	55.2 g/L	ALOGPS
logP	1.56	ALOGPS
logP	0.99	ChemAxon
logS	-0.42	ALOGPS
pKa (Strongest Acidic)	12.6	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	37.59 m³·mol⁻¹	ChemAxon
Polarizability	15.82 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]+	133.146	31661259
DarkChem	[M-H]-	128.497	31661259
DeepCCS	[M+H]+	132.797	30932474
DeepCCS	[M-H]-	129.061	30932474
DeepCCS	[M-2H]-	166.561	30932474
DeepCCS	[M+Na]+	141.836	30932474
AllCCS	[M+H]+	135.1	32859911
AllCCS	[M+H-H2O]+	131.1	32859911
AllCCS	[M+NH4]+	138.8	32859911
AllCCS	[M+Na]+	139.9	32859911
AllCCS	[M-H]-	133.9	32859911
AllCCS	[M+Na-2H]-	136.4	32859911
AllCCS	[M+HCOO]-	139.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+/-)-Ethyl 2-hydroxy-2-methylbutyrate	CCOC(=O)C(C)(O)CC	1390.2	Standard polar	33892256
(+/-)-Ethyl 2-hydroxy-2-methylbutyrate	CCOC(=O)C(C)(O)CC	976.2	Standard non polar	33892256
(+/-)-Ethyl 2-hydroxy-2-methylbutyrate	CCOC(=O)C(C)(O)CC	970.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+/-)-Ethyl 2-hydroxy-2-methylbutyrate,1TMS,isomer #1	CCOC(=O)C(C)(CC)O[Si](C)(C)C	1095.7	Semi standard non polar	33892256
(+/-)-Ethyl 2-hydroxy-2-methylbutyrate,1TBDMS,isomer #1	CCOC(=O)C(C)(CC)O[Si](C)(C)C(C)(C)C	1322.1	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 - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9000000000-8dd8260e9a370d6972c1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate GC-MS (1 TMS) - 70eV, Positive	splash10-0002-5900000000-9b79de02b976703ef61f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 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 - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 10V, Positive-QTOF	splash10-0002-1900000000-f482183144bb01e53b89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 20V, Positive-QTOF	splash10-0fba-9600000000-4401d6e3de5216608c8f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 40V, Positive-QTOF	splash10-0pir-9000000000-f3978e33515afcdc009b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 10V, Negative-QTOF	splash10-0002-4900000000-76a1f4a752a614bde6c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 20V, Negative-QTOF	splash10-006t-9500000000-f8a063b33decdda91fa8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 40V, Negative-QTOF	splash10-05fr-9000000000-aafd6ca9d1b8107ed736	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 10V, Positive-QTOF	splash10-0a4i-9200000000-f6aa5dc70fe5cc55c871	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 20V, Positive-QTOF	splash10-0a4i-9000000000-ae82af5a5103e426f1fb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 40V, Positive-QTOF	splash10-0a4i-9000000000-1ea58d5a361481465a4f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 10V, Negative-QTOF	splash10-00kb-9600000000-2d32736502960e800cd1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 20V, Negative-QTOF	splash10-00ke-9400000000-ff1ca3847b0b15d441b7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-2-methylbutyrate 40V, Negative-QTOF	splash10-0604-9000000000-d34b42291d1df46612aa	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB009393

KNApSAcK ID

Not Available

Chemspider ID

91747

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101536

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

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 ]
(). EAFUS: Everything Added to Food in the United States.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (+/-)-Ethyl 2-hydroxy-2-methylbutyrate (HMDB0032269)

MOL for HMDB0032269 ((+/-)-Ethyl 2-hydroxy-2-methylbutyrate)

3D MOL for HMDB0032269 ((+/-)-Ethyl 2-hydroxy-2-methylbutyrate)

3D SDF for HMDB0032269 ((+/-)-Ethyl 2-hydroxy-2-methylbutyrate)

3D-SDF for HMDB0032269 ((+/-)-Ethyl 2-hydroxy-2-methylbutyrate)

PDB for HMDB0032269 ((+/-)-Ethyl 2-hydroxy-2-methylbutyrate)

3D PDB for HMDB0032269 ((+/-)-Ethyl 2-hydroxy-2-methylbutyrate)

SMILES for HMDB0032269 ((+/-)-Ethyl 2-hydroxy-2-methylbutyrate)

INCHI for HMDB0032269 ((+/-)-Ethyl 2-hydroxy-2-methylbutyrate)

Structure for HMDB0032269 ((+/-)-Ethyl 2-hydroxy-2-methylbutyrate)

3D Structure for HMDB0032269 ((+/-)-Ethyl 2-hydroxy-2-methylbutyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra