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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:57:22 UTC

Update Date

2023-02-21 17:23:56 UTC

HMDB ID

HMDB0034161

Secondary Accession Numbers

HMDB34161

Metabolite Identification

Common Name

2-Methylpropyl butanoate

Description

2-Methylpropyl butanoate, also known as butyric acid, isobutyl ester or isobutyl butanoate, 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 significant number of articles have been published on 2-Methylpropyl butanoate.

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-Methyl-1-propyl butyrate	ChEBI
2-Methylpropyl butyrate	ChEBI
Butanoic acid, 2-methylpropyl ester	ChEBI
Butanoic acid, isobutyl ester	ChEBI
Butanoic acid, methyl propyl ester	ChEBI
Butyric acid, isobutyl ester	ChEBI
Isobutyl butanoate	ChEBI
Isobutyl N-butyrate	ChEBI
2-Methyl-1-propyl butyric acid	Generator
2-Methylpropyl butyric acid	Generator
Butanoate, 2-methylpropyl ester	Generator
Butanoate, isobutyl ester	Generator
Butanoate, methyl propyl ester	Generator
Butyrate, isobutyl ester	Generator
Isobutyl butanoic acid	Generator
Isobutyl N-butyric acid	Generator
2-Methylpropyl butanoic acid	Generator
FEMA 2187	HMDB
Isobutyl butyrate	HMDB
Isobutyl ester OF butanoic acid	HMDB
Isobutyl-N-butyrate	HMDB
N-Butyric acid isobutyl ester	HMDB

Chemical Formula

C₈H₁₆O₂

Average Molecular Weight

144.2114

Monoisotopic Molecular Weight

144.115029756

IUPAC Name

2-methylpropyl butanoate

Traditional Name

2-methylpropyl butanoate

CAS Registry Number

539-90-2

SMILES

CCCC(=O)OCC(C)C

InChI Identifier

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

InChI Key

RGFNRWTWDWVHDD-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

butyrate ester (CHEBI:87683 )

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Feces (PMID: 23454028)
Urine (HMDB: HMDB0034161)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034161)

Source

Endogenous

Endogenous (HMDB: HMDB0034161)

Plant

Plant (HMDB: HMDB0034161)

Animal

Animal (HMDB: HMDB0034161)

Exogenous

Food

Food (HMDB: HMDB0034161)

Fruit

Pome

Apple (FooDB: FOOD00105)
Asian pear (FooDB: FOOD00291)

Fruits (FooDB: FOOD00871)

Herb and spice

Herb

Roman camomile (FooDB: FOOD00046)

Exogenous (HMDB: HMDB0034161)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034161)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034161)

Lipid metabolism pathway (HMDB: HMDB0034161)

Cellular process

Cell signaling (HMDB: HMDB0034161)

Biochemical process

Lipid transport (HMDB: HMDB0034161)

Role

Biological role

Energy source (HMDB: HMDB0034161)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034161)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	156.90 °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	2.760	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.72 g/L	ALOGPS
logP	2.65	ALOGPS
logP	2.31	ChemAxon
logS	-1.9	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	40.38 m³·mol⁻¹	ChemAxon
Polarizability	17.06 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]+	133.051	31661259
DarkChem	[M-H]-	130.144	31661259
DeepCCS	[M+H]+	134.963	30932474
DeepCCS	[M-H]-	132.063	30932474
DeepCCS	[M-2H]-	168.821	30932474
DeepCCS	[M+Na]+	144.017	30932474
AllCCS	[M+H]+	135.2	32859911
AllCCS	[M+H-H2O]+	131.2	32859911
AllCCS	[M+NH4]+	138.8	32859911
AllCCS	[M+Na]+	139.9	32859911
AllCCS	[M-H]-	136.3	32859911
AllCCS	[M+Na-2H]-	138.9	32859911
AllCCS	[M+HCOO]-	141.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methylpropyl butanoate	CCCC(=O)OCC(C)C	1173.5	Standard polar	33892256
2-Methylpropyl butanoate	CCCC(=O)OCC(C)C	919.5	Standard non polar	33892256
2-Methylpropyl butanoate	CCCC(=O)OCC(C)C	960.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl butanoate EI-B (Non-derivatized)	splash10-05fu-9000000000-8ca43e86a485b4a1debf	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl butanoate EI-B (Non-derivatized)	splash10-05fu-9000000000-caf15cc81f8fd2a7531f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl butanoate EI-B (Non-derivatized)	splash10-05fr-9000000000-89a8fa52be9941be8e10	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl butanoate EI-B (Non-derivatized)	splash10-05fu-9000000000-8ca43e86a485b4a1debf	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl butanoate EI-B (Non-derivatized)	splash10-05fu-9000000000-caf15cc81f8fd2a7531f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl butanoate EI-B (Non-derivatized)	splash10-05fr-9000000000-89a8fa52be9941be8e10	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylpropyl butanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-9000000000-90bafdff80f05fa2d929	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylpropyl butanoate 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-Methylpropyl butanoate 10V, Positive-QTOF	splash10-052b-9600000000-704be4ab2fbc7786d081	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl butanoate 20V, Positive-QTOF	splash10-0a4i-9000000000-d6ac55edd63a3c7e3840	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl butanoate 40V, Positive-QTOF	splash10-0a4i-9000000000-7a53998366f3c0bb5126	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl butanoate 10V, Negative-QTOF	splash10-00kf-9800000000-ec011f1d1a1b1f8c0a31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl butanoate 20V, Negative-QTOF	splash10-014u-9100000000-39699396fa1e041b3b24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl butanoate 40V, Negative-QTOF	splash10-00kf-9000000000-540d4752e7b44a702690	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl butanoate 10V, Positive-QTOF	splash10-0ab9-9000000000-8f5d90fcaef5ee242eed	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl butanoate 20V, Positive-QTOF	splash10-0a4i-9000000000-8e7720f9b2ec0ec223c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl butanoate 40V, Positive-QTOF	splash10-052f-9000000000-e76a05675133caebfa74	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl butanoate 10V, Negative-QTOF	splash10-00di-9100000000-fe1a1b96af64753dc1b3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl butanoate 20V, Negative-QTOF	splash10-014u-9100000000-b908ec6cc4138f94c8e7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl butanoate 40V, Negative-QTOF	splash10-014i-9000000000-d1633ce20917ac544b2d	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

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	Diarrhea-predominant IBS	23516449	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 ]
Diarrhoea predominant irritable bowel syndrome
Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012447

KNApSAcK ID

Not Available

Chemspider ID

10423

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10885

PDB ID

Not Available

ChEBI ID

87683

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1012391

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 2-Methylpropyl butanoate (HMDB0034161)

MOL for HMDB0034161 (2-Methylpropyl butanoate)

3D MOL for HMDB0034161 (2-Methylpropyl butanoate)

3D SDF for HMDB0034161 (2-Methylpropyl butanoate)

3D-SDF for HMDB0034161 (2-Methylpropyl butanoate)

PDB for HMDB0034161 (2-Methylpropyl butanoate)

3D PDB for HMDB0034161 (2-Methylpropyl butanoate)

SMILES for HMDB0034161 (2-Methylpropyl butanoate)

INCHI for HMDB0034161 (2-Methylpropyl butanoate)

Structure for HMDB0034161 (2-Methylpropyl butanoate)

3D Structure for HMDB0034161 (2-Methylpropyl butanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra