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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:34:17 UTC

Update Date

2023-02-21 17:19:25 UTC

HMDB ID

HMDB0030027

Secondary Accession Numbers

HMDB30027

Metabolite Identification

Common Name

Methyl 3-methylbutanoate

Description

Methyl 3-methylbutanoate belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group. Based on a literature review a small amount of articles have been published on Methyl 3-methylbutanoate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl 3-methylbutanoic acid	Generator
3-Methyl-2-oxobutanoic acid	HMDB
3-Methylbutanoic acid methyl ester	HMDB
Butanoic acid, 3-methyl-, methyl ester	HMDB
FEMA 2753	HMDB
Isovaleric acid, methyl ester	HMDB
Methyl 3-methylbutyrate	HMDB
Methyl isopentanoate	HMDB
Methyl isovalerate	HMDB
Methyl isovalerianate	HMDB

Chemical Formula

C₆H₁₂O₂

Average Molecular Weight

116.1583

Monoisotopic Molecular Weight

116.083729628

IUPAC Name

methyl 3-methylbutanoate

Traditional Name

methyl (3-methyl)butanoate

CAS Registry Number

556-24-1

SMILES

COC(=O)CC(C)C

InChI Identifier

InChI=1S/C6H12O2/c1-5(2)4-6(7)8-3/h5H,4H2,1-3H3

InChI Key

OQAGVSWESNCJJT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid methyl esters

Alternative Parents

Substituents

Fatty acid methyl ester
Methyl 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 (HMDB: HMDB0030027)
Urine (HMDB: HMDB0030027)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030027)

Source

Endogenous

Endogenous (HMDB: HMDB0030027)

Plant

Plant (HMDB: HMDB0030027)
Fabaceae (HMDB: HMDB0030027)

Animal

Animal (HMDB: HMDB0030027)

Exogenous

Food

Food (HMDB: HMDB0030027)

Fruit

Tropical fruit

Pineapple (FooDB: FOOD00012)

Berry

Pome

Pomes (FooDB: FOOD00856)

Citrus

Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Herb and spice

Herb

Common sage (FooDB: FOOD00165)

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030027)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030027)

Cellular process

Cell signaling (HMDB: HMDB0030027)

Biochemical process

Lipid transport (HMDB: HMDB0030027)

Role

Biological role

Energy storage (HMDB: HMDB0030027)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030027)

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0030027)
Flavoring Agent (HMDB: HMDB0030027)

Fragrance (HMDB: HMDB0030027)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	114.00 to 115.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2892 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.82	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.75 g/L	ALOGPS
logP	1.62	ALOGPS
logP	1.35	ChemAxon
logS	-1.1	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	3	ChemAxon
Refractivity	31.19 m³·mol⁻¹	ChemAxon
Polarizability	12.98 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]+	126.877	31661259
DarkChem	[M-H]-	121.354	31661259
DeepCCS	[M+H]+	130.081	30932474
DeepCCS	[M-H]-	127.773	30932474
DeepCCS	[M-2H]-	163.931	30932474
DeepCCS	[M+Na]+	138.921	30932474
AllCCS	[M+H]+	128.0	32859911
AllCCS	[M+H-H2O]+	123.8	32859911
AllCCS	[M+NH4]+	131.9	32859911
AllCCS	[M+Na]+	133.0	32859911
AllCCS	[M-H]-	128.8	32859911
AllCCS	[M+Na-2H]-	132.2	32859911
AllCCS	[M+HCOO]-	136.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl 3-methylbutanoate	COC(=O)CC(C)C	994.0	Standard polar	33892256
Methyl 3-methylbutanoate	COC(=O)CC(C)C	763.0	Standard non polar	33892256
Methyl 3-methylbutanoate	COC(=O)CC(C)C	800.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methyl 3-methylbutanoate EI-B (Non-derivatized)	splash10-0596-9000000000-07204361bb9951b4e592	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl 3-methylbutanoate CI-B (Non-derivatized)	splash10-014i-1900000000-73589b5b124cd5952eb4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl 3-methylbutanoate EI-B (Non-derivatized)	splash10-00dl-9000000000-7f5aff59c48fa693bf95	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl 3-methylbutanoate EI-B (Non-derivatized)	splash10-0596-9000000000-07204361bb9951b4e592	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl 3-methylbutanoate CI-B (Non-derivatized)	splash10-014i-1900000000-73589b5b124cd5952eb4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl 3-methylbutanoate EI-B (Non-derivatized)	splash10-00dl-9000000000-7f5aff59c48fa693bf95	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 3-methylbutanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9100000000-3ff699d2c612b060724a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 3-methylbutanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 3-methylbutanoate 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 - Methyl 3-methylbutanoate 10V, Positive-QTOF	splash10-014r-9500000000-9a850cea31d510c0fd2f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-methylbutanoate 20V, Positive-QTOF	splash10-0006-9100000000-df05a91c6a1411debb0b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-methylbutanoate 40V, Positive-QTOF	splash10-052f-9000000000-163b5d248d223ef6a091	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-methylbutanoate 10V, Negative-QTOF	splash10-014i-5900000000-3d6c7f2a23147213d6c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-methylbutanoate 20V, Negative-QTOF	splash10-0159-9600000000-47805aaec95d0313c5ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-methylbutanoate 40V, Negative-QTOF	splash10-05o3-9000000000-a3fffdc9068f90db5da6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-methylbutanoate 10V, Negative-QTOF	splash10-0159-4900000000-b71bf30facabe23ac72b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-methylbutanoate 20V, Negative-QTOF	splash10-001i-9100000000-59e583f996e46c254a48	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-methylbutanoate 40V, Negative-QTOF	splash10-00kf-9000000000-deeb5ac0dae597e862c6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-methylbutanoate 10V, Positive-QTOF	splash10-05mx-9100000000-5c09c98f52aa9459e417	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-methylbutanoate 20V, Positive-QTOF	splash10-0006-9000000000-aef3389e6457a396e1c2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 3-methylbutanoate 40V, Positive-QTOF	splash10-0006-9000000000-239c364de1bc6d5eb7ad	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20055983	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
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	Clostridium difficile infection	17314143	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

FDB001325

KNApSAcK ID

Not Available

Chemspider ID

10687

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11160

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1021171

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 Methyl 3-methylbutanoate (HMDB0030027)

MOL for HMDB0030027 (Methyl 3-methylbutanoate)

3D MOL for HMDB0030027 (Methyl 3-methylbutanoate)

3D SDF for HMDB0030027 (Methyl 3-methylbutanoate)

3D-SDF for HMDB0030027 (Methyl 3-methylbutanoate)

PDB for HMDB0030027 (Methyl 3-methylbutanoate)

3D PDB for HMDB0030027 (Methyl 3-methylbutanoate)

SMILES for HMDB0030027 (Methyl 3-methylbutanoate)

INCHI for HMDB0030027 (Methyl 3-methylbutanoate)

Structure for HMDB0030027 (Methyl 3-methylbutanoate)

3D Structure for HMDB0030027 (Methyl 3-methylbutanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra