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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-03-07 21:33:57 UTC

Update Date

2023-02-21 17:29:31 UTC

HMDB ID

HMDB0059867

Secondary Accession Numbers

HMDB59867

Metabolite Identification

Common Name

Ethyl 2-hydroxy-4-methylpentanoate

Description

Ethyl 2-hydroxy-4-methylpentanoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Ethyl 2-hydroxy-4-methylpentanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

COMPND    HMDB0059867
HETATM    1  C1  UNL     1       4.432   0.573   0.117  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.521  -0.590  -0.123  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.181  -0.127  -0.348  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.140  -1.010  -0.596  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.416  -2.235  -0.616  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.241  -0.545  -0.830  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.053  -1.656  -1.048  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.808   0.260   0.287  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.216   0.669  -0.088  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.141  -0.482  -0.332  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.822   1.600   0.937  1.00  0.00           C  
HETATM   12  H1  UNL     1       5.452   0.288  -0.222  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.412   0.796   1.206  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.041   1.438  -0.485  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.830  -1.070  -1.081  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.551  -1.337   0.689  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.266   0.065  -1.752  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.841  -2.068  -1.922  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.832  -0.283   1.255  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.240   1.215   0.449  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.195   1.261  -1.051  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.189  -0.809  -1.397  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.918  -1.339   0.305  1.00  0.00           H  
HETATM   24  H13 UNL     1      -4.181  -0.095  -0.117  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.249   2.521   0.489  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.696   1.086   1.436  1.00  0.00           H  
HETATM   27  H16 UNL     1      -2.085   1.874   1.713  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   19   20
CONECT    9   10   11   21
CONECT   10   22   23   24
CONECT   11   25   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyl 2-hydroxy-4-methylpentanoic acid	Generator
Ethyl 2-hydroxy-4-methylpentanoate	MeSH
Ethyl DL-leucic acid	Generator

Chemical Formula

C₈H₁₆O₃

Average Molecular Weight

160.2108

Monoisotopic Molecular Weight

160.109944378

IUPAC Name

ethyl 2-hydroxy-4-methylpentanoate

Traditional Name

ethyl 2-hydroxy-4-methylpentanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

QRHOWVDPHIXNEN-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
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

Not Available

Not Available

Not Available

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	27.6 g/L	ALOGPS
logP	1.39	ALOGPS
logP	1.28	ChemAxon
logS	-0.76	ALOGPS
pKa (Strongest Acidic)	12.7	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	5	ChemAxon
Refractivity	42.03 m³·mol⁻¹	ChemAxon
Polarizability	18.02 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]+	136.368	31661259
DarkChem	[M-H]-	133.657	31661259
DeepCCS	[M+H]+	138.984	30932474
DeepCCS	[M-H]-	136.172	30932474
DeepCCS	[M-2H]-	172.616	30932474
DeepCCS	[M+Na]+	148.137	30932474
AllCCS	[M+H]+	138.6	32859911
AllCCS	[M+H-H2O]+	134.7	32859911
AllCCS	[M+NH4]+	142.2	32859911
AllCCS	[M+Na]+	143.2	32859911
AllCCS	[M-H]-	138.3	32859911
AllCCS	[M+Na-2H]-	140.4	32859911
AllCCS	[M+HCOO]-	142.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 2-hydroxy-4-methylpentanoate	CCOC(=O)C(O)CC(C)C	1500.9	Standard polar	33892256
Ethyl 2-hydroxy-4-methylpentanoate	CCOC(=O)C(O)CC(C)C	1070.9	Standard non polar	33892256
Ethyl 2-hydroxy-4-methylpentanoate	CCOC(=O)C(O)CC(C)C	1090.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 2-hydroxy-4-methylpentanoate,1TMS,isomer #1	CCOC(=O)C(CC(C)C)O[Si](C)(C)C	1186.7	Semi standard non polar	33892256
Ethyl 2-hydroxy-4-methylpentanoate,1TBDMS,isomer #1	CCOC(=O)C(CC(C)C)O[Si](C)(C)C(C)(C)C	1388.0	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-4-methylpentanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-9000000000-e1d259147be8622c594c	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate GC-MS (1 TMS) - 70eV, Positive	splash10-0a4l-9700000000-835f377d194e9fefe695	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate 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-4-methylpentanoate 10V, Positive-QTOF	splash10-03di-3900000000-2a09ef63a0d9d74dd695	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate 20V, Positive-QTOF	splash10-0aos-9400000000-d8f5b8d4132c8acd3887	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate 40V, Positive-QTOF	splash10-0a4i-9000000000-265367a31da3b70d519a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate 10V, Negative-QTOF	splash10-0bt9-3900000000-f8044c2d854ce7567625	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate 20V, Negative-QTOF	splash10-08fs-9600000000-a17e2fdc0d95f483af26	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate 40V, Negative-QTOF	splash10-052k-9000000000-59c1fc0236e04ec2d29d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate 10V, Positive-QTOF	splash10-00kr-9000000000-adeb74c8b01969bdf824	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate 20V, Positive-QTOF	splash10-014i-9000000000-16784f10cafd9f1d6c3b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate 40V, Positive-QTOF	splash10-0006-9000000000-ee8a9a0d1f3a3302f7ae	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate 10V, Negative-QTOF	splash10-0a4i-0900000000-82c1b5bbb6dbc56b4d94	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate 20V, Negative-QTOF	splash10-000m-9200000000-950250f021182d4a9a2f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-hydroxy-4-methylpentanoate 40V, Negative-QTOF	splash10-014r-9000000000-dfcb78be88ca2e48c3a4	2021-10-11	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

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

112030

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 ]
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-4-methylpentanoate (HMDB0059867)

MOL for HMDB0059867 (Ethyl 2-hydroxy-4-methylpentanoate)

3D MOL for HMDB0059867 (Ethyl 2-hydroxy-4-methylpentanoate)

3D SDF for HMDB0059867 (Ethyl 2-hydroxy-4-methylpentanoate)

3D-SDF for HMDB0059867 (Ethyl 2-hydroxy-4-methylpentanoate)

PDB for HMDB0059867 (Ethyl 2-hydroxy-4-methylpentanoate)

3D PDB for HMDB0059867 (Ethyl 2-hydroxy-4-methylpentanoate)

SMILES for HMDB0059867 (Ethyl 2-hydroxy-4-methylpentanoate)

INCHI for HMDB0059867 (Ethyl 2-hydroxy-4-methylpentanoate)

Structure for HMDB0059867 (Ethyl 2-hydroxy-4-methylpentanoate)

3D Structure for HMDB0059867 (Ethyl 2-hydroxy-4-methylpentanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra