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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

2022-03-07 02:53:18 UTC

HMDB ID

HMDB0032270

Secondary Accession Numbers

HMDB32270

Metabolite Identification

Common Name

(+/-)-Ethyl 2-hydroxy-3-methylvalerate

Description

(+/-)-Ethyl 2-hydroxy-3-methylvalerate 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-3-methylvalerate.

Structure

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

COMPND    HMDB0032270
HETATM    1  C1  UNL     1      -4.226   0.289   1.006  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.125   0.581  -0.003  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.848   0.420   0.580  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.738   0.648  -0.203  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.908   0.986  -1.395  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.604   0.495   0.354  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.636   0.121   1.672  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.376  -0.456  -0.542  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.734  -1.808  -0.633  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.837  -0.531  -0.170  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.488   0.829  -0.284  1.00  0.00           C  
HETATM   12  H1  UNL     1      -4.261   1.159   1.689  1.00  0.00           H  
HETATM   13  H2  UNL     1      -5.182   0.105   0.479  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.982  -0.644   1.564  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.239  -0.125  -0.864  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.283   1.597  -0.423  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.157   1.479   0.285  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.242   0.003   2.092  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.334  -0.003  -1.571  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.050  -1.851  -1.426  1.00  0.00           H  
HETATM   21  H10 UNL     1       1.516  -2.538  -0.934  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.233  -2.102   0.311  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.323  -1.229  -0.853  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.971  -0.915   0.868  1.00  0.00           H  
HETATM   25  H14 UNL     1       4.590   0.693  -0.311  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.108   1.327  -1.203  1.00  0.00           H  
HETATM   27  H16 UNL     1       3.177   1.471   0.576  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    8   17
CONECT    7   18
CONECT    8    9   10   19
CONECT    9   20   21   22
CONECT   10   11   23   24
CONECT   11   25   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+/-)-ethyl 2-hydroxy-3-methylvaleric acid	Generator

Chemical Formula

C₈H₁₆O₃

Average Molecular Weight

160.2108

Monoisotopic Molecular Weight

160.109944378

IUPAC Name

ethyl 2-hydroxy-3-methylpentanoate

Traditional Name

ethyl 2-hydroxy-3-methylpentanoate

CAS Registry Number

24323-38-4

SMILES

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

InChI Identifier

InChI=1S/C8H16O3/c1-4-6(3)7(9)8(10)11-5-2/h6-7,9H,4-5H2,1-3H3

InChI Key

TXLBCYISDOYPIH-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
Monosaccharide
Secondary 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

Cell membrane (HMDB: HMDB0032270)

Biofluid or Excreta

Urine (HMDB: HMDB0032270)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032270)

Source

Endogenous

Endogenous (HMDB: HMDB0032270)

Animal

Animal (HMDB: HMDB0032270)

Exogenous

Food

Food (HMDB: HMDB0032270)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0032270)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0032270)

Cellular process

Cell signaling (HMDB: HMDB0032270)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0032270)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0032270)

Nutrient

Nutrient (HMDB: HMDB0032270)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032270)

Emulsifier (HMDB: HMDB0032270)

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	26 g/L	ALOGPS
logP	1.5	ALOGPS
logP	1.36	ChemAxon
logS	-0.79	ALOGPS
pKa (Strongest Acidic)	12.48	ChemAxon
pKa (Strongest Basic)	-3.9	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	5	ChemAxon
Refractivity	41.95 m³·mol⁻¹	ChemAxon
Polarizability	17.78 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	136.717	31661259
DarkChem	[M-H]-	133.442	31661259
DeepCCS	[M+H]+	137.647	30932474
DeepCCS	[M-H]-	134.93	30932474
DeepCCS	[M-2H]-	171.331	30932474
DeepCCS	[M+Na]+	146.738	30932474
AllCCS	[M+H]+	139.1	32859911
AllCCS	[M+H-H2O]+	135.2	32859911
AllCCS	[M+NH4]+	142.8	32859911
AllCCS	[M+Na]+	143.8	32859911
AllCCS	[M-H]-	138.4	32859911
AllCCS	[M+Na-2H]-	140.5	32859911
AllCCS	[M+HCOO]-	142.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+/-)-Ethyl 2-hydroxy-3-methylvalerate	CCOC(=O)C(O)C(C)CC	1529.0	Standard polar	33892256
(+/-)-Ethyl 2-hydroxy-3-methylvalerate	CCOC(=O)C(O)C(C)CC	1105.7	Standard non polar	33892256
(+/-)-Ethyl 2-hydroxy-3-methylvalerate	CCOC(=O)C(O)C(C)CC	1101.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+/-)-Ethyl 2-hydroxy-3-methylvalerate,1TMS,isomer #1	CCOC(=O)C(O[Si](C)(C)C)C(C)CC	1204.8	Semi standard non polar	33892256
(+/-)-Ethyl 2-hydroxy-3-methylvalerate,1TBDMS,isomer #1	CCOC(=O)C(O[Si](C)(C)C(C)(C)C)C(C)CC	1415.2	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-3-methylvalerate GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9000000000-4a4882083418b7525d74	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9710000000-7d3a029e54e11ba0071a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate 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-3-methylvalerate 10V, Positive-QTOF	splash10-03di-4900000000-e125758cdcda593f9ff6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate 20V, Positive-QTOF	splash10-0a4i-9200000000-bb83c48cee34da4aab9a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate 40V, Positive-QTOF	splash10-0a4i-9000000000-3a167e1eea8daaf3e7e0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate 10V, Negative-QTOF	splash10-0a4i-5900000000-28d12bb3e2d4ad5a17fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate 20V, Negative-QTOF	splash10-08fs-9700000000-09972f2584be2e8f3169	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate 40V, Negative-QTOF	splash10-0a4j-9000000000-fdb911eccdcc68d26cb7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate 10V, Positive-QTOF	splash10-00kr-9600000000-cff1093c88c3fee15c86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate 20V, Positive-QTOF	splash10-014i-9000000000-9c7c815b0f831377d0c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate 40V, Positive-QTOF	splash10-0aou-9000000000-a0c6ddff6a55aa5ced6e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate 10V, Negative-QTOF	splash10-0a4i-0900000000-8f721ac0687e64e8b9a1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate 20V, Negative-QTOF	splash10-03dl-9600000000-f9684d298d550276b134	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+/-)-Ethyl 2-hydroxy-3-methylvalerate 40V, Negative-QTOF	splash10-0005-9200000000-9bb8d8ddb9539c92a771	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

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

FDB009394

KNApSAcK ID

Not Available

Chemspider ID

13658708

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13026600

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-3-methylvalerate (HMDB0032270)

MOL for HMDB0032270 ((+/-)-Ethyl 2-hydroxy-3-methylvalerate)

3D MOL for HMDB0032270 ((+/-)-Ethyl 2-hydroxy-3-methylvalerate)

3D SDF for HMDB0032270 ((+/-)-Ethyl 2-hydroxy-3-methylvalerate)

3D-SDF for HMDB0032270 ((+/-)-Ethyl 2-hydroxy-3-methylvalerate)

PDB for HMDB0032270 ((+/-)-Ethyl 2-hydroxy-3-methylvalerate)

3D PDB for HMDB0032270 ((+/-)-Ethyl 2-hydroxy-3-methylvalerate)

SMILES for HMDB0032270 ((+/-)-Ethyl 2-hydroxy-3-methylvalerate)

INCHI for HMDB0032270 ((+/-)-Ethyl 2-hydroxy-3-methylvalerate)

Structure for HMDB0032270 ((+/-)-Ethyl 2-hydroxy-3-methylvalerate)

3D Structure for HMDB0032270 ((+/-)-Ethyl 2-hydroxy-3-methylvalerate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra