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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:48:52 UTC

Update Date

2023-02-21 17:21:50 UTC

HMDB ID

HMDB0032272

Secondary Accession Numbers

HMDB32272

Metabolite Identification

Common Name

Ethyl 4-methylpentanoate

Description

Ethyl 4-methylpentanoate 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 4-methylpentanoate.

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 4-methylpentanoic acid	Generator
Ethyl 4-methylvalerate	HMDB
Ethyl isocaproate	HMDB
Ethyl isohexanoate	HMDB
Pentanoic acid, 4-methyl-, ethyl ester	HMDB
Valeric acid, 4-methyl-, ethyl ester	HMDB

Chemical Formula

C₈H₁₆O₂

Average Molecular Weight

144.2114

Monoisotopic Molecular Weight

144.115029756

IUPAC Name

ethyl 4-methylpentanoate

Traditional Name

ethyl 4-methylpentanoate

CAS Registry Number

25415-67-2

SMILES

CCOC(=O)CCC(C)C

InChI Identifier

InChI=1S/C8H16O2/c1-4-10-8(9)6-5-7(2)3/h7H,4-6H2,1-3H3

InChI Key

OFQRUTMGVBMTFQ-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
Carboxylic acid ester
Monocarboxylic acid or derivatives
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

Cellular substructure

Excreta

Biofluid or Excreta

Feces (PMID: 23454028)
Urine (HMDB: HMDB0032272)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032272)

Source

Endogenous

Endogenous (HMDB: HMDB0032272)

Animal

Animal (HMDB: HMDB0032272)

Exogenous

Food

Food (HMDB: HMDB0032272)

Exogenous (HMDB: HMDB0032272)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032272)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032272)

Lipid metabolism pathway (HMDB: HMDB0032272)

Cellular process

Cell signaling (HMDB: HMDB0032272)

Biochemical process

Lipid transport (HMDB: HMDB0032272)

Role

Biological role

Energy source (HMDB: HMDB0032272)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032272)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	160.00 to 163.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	356.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.667 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.59 g/L	ALOGPS
logP	2.64	ALOGPS
logP	2.16	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.54 m³·mol⁻¹	ChemAxon
Polarizability	17.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.566	31661259
DarkChem	[M-H]-	130.228	31661259
DeepCCS	[M+H]+	136.786	30932474
DeepCCS	[M-H]-	133.751	30932474
DeepCCS	[M-2H]-	170.541	30932474
DeepCCS	[M+Na]+	145.805	30932474
AllCCS	[M+H]+	134.6	32859911
AllCCS	[M+H-H2O]+	130.6	32859911
AllCCS	[M+NH4]+	138.4	32859911
AllCCS	[M+Na]+	139.4	32859911
AllCCS	[M-H]-	136.1	32859911
AllCCS	[M+Na-2H]-	138.5	32859911
AllCCS	[M+HCOO]-	141.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 4-methylpentanoate	CCOC(=O)CCC(C)C	1188.7	Standard polar	33892256
Ethyl 4-methylpentanoate	CCOC(=O)CCC(C)C	944.3	Standard non polar	33892256
Ethyl 4-methylpentanoate	CCOC(=O)CCC(C)C	976.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Ethyl 4-methylpentanoate EI-B (Non-derivatized)	splash10-0f9g-9100000000-4bbceed47a2856975b25	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl 4-methylpentanoate EI-B (Non-derivatized)	splash10-0f9g-9100000000-4bbceed47a2856975b25	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 4-methylpentanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-9000000000-3b07b69d94c9b6eb4a94	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 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 4-methylpentanoate 10V, Positive-QTOF	splash10-0002-5900000000-d175ba1ac3cf038d09ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-methylpentanoate 20V, Positive-QTOF	splash10-0002-9200000000-beb51ff7539f35291924	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-methylpentanoate 40V, Positive-QTOF	splash10-0a4i-9000000000-2f0529a99b024483ad34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-methylpentanoate 10V, Negative-QTOF	splash10-0007-7900000000-7e41e6856fc670e37505	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-methylpentanoate 20V, Negative-QTOF	splash10-0002-9300000000-68935c85de8144a5dbb5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-methylpentanoate 40V, Negative-QTOF	splash10-052e-9000000000-0a132fb2aea82f059d79	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-methylpentanoate 10V, Negative-QTOF	splash10-00kb-9800000000-2adfd5aa1ca20dfbc185	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-methylpentanoate 20V, Negative-QTOF	splash10-0002-9100000000-8bf1367a2f59795bb5a5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-methylpentanoate 40V, Negative-QTOF	splash10-0002-9000000000-c281ac3403859ce46c9e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-methylpentanoate 10V, Positive-QTOF	splash10-0592-9100000000-3e9621c74ef3abef6997	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-methylpentanoate 20V, Positive-QTOF	splash10-0592-9000000000-c91de8cf5de78d0d8768	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-methylpentanoate 40V, Positive-QTOF	splash10-0536-9000000000-baec6291091a844f95d6	2021-09-23	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

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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details

Associated Disorders and Diseases

Disease References

Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB009400

KNApSAcK ID

C00050448

Chemspider ID

104984

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

117477

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1477041

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 4-methylpentanoate (HMDB0032272)

MOL for HMDB0032272 (Ethyl 4-methylpentanoate)

3D MOL for HMDB0032272 (Ethyl 4-methylpentanoate)

3D SDF for HMDB0032272 (Ethyl 4-methylpentanoate)

3D-SDF for HMDB0032272 (Ethyl 4-methylpentanoate)

PDB for HMDB0032272 (Ethyl 4-methylpentanoate)

3D PDB for HMDB0032272 (Ethyl 4-methylpentanoate)

SMILES for HMDB0032272 (Ethyl 4-methylpentanoate)

INCHI for HMDB0032272 (Ethyl 4-methylpentanoate)

Structure for HMDB0032272 (Ethyl 4-methylpentanoate)

3D Structure for HMDB0032272 (Ethyl 4-methylpentanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra