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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:41 UTC

Update Date

2023-02-21 17:20:06 UTC

HMDB ID

HMDB0031221

Secondary Accession Numbers

HMDB31221

Metabolite Identification

Common Name

2-Ethylbutanoic acid

Description

2-Ethylbutanoic acid, also known as 2-ethylbutanoate, belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain. Based on a literature review a small amount of articles have been published on 2-Ethylbutanoic acid.

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-Ethylbutanoate	Generator
2-Ethyl-butyric acid	ChEMBL, HMDB
2-Ethyl-butyrate	Generator, HMDB
(C2H5)2chcooh	HMDB
2-Ethyl butanoic acid	HMDB
2-Ethyl-butanoic acid	HMDB
2-Ethyl-N-butyric acid	HMDB
2-Ethylbutyric acid	HMDB
2-Ethylbutyric acid, 8ci	HMDB
3-Pentane-carboxylic acid	HMDB
3-Pentanecarboxylic acid	HMDB
a-Ethylbutyric acid	HMDB
alpha-Ethylbutyric acid	HMDB
alpha-Ethylbuytyric acid	HMDB
Diethyl acetic acid	HMDB
Diethyl-acetic acid	HMDB
Diethylacetic acid	HMDB
FEMA 2429	HMDB
Pentane-3-carboxylic acid	HMDB
Diethyl acetate	Generator

Chemical Formula

C₆H₁₂O₂

Average Molecular Weight

116.1583

Monoisotopic Molecular Weight

116.083729628

IUPAC Name

2-ethylbutanoic acid

Traditional Name

2-ethylbutyric acid

CAS Registry Number

88-09-5

SMILES

CCC(CC)C(O)=O

InChI Identifier

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

InChI Key

OXQGTIUCKGYOAA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Branched fatty acids

Alternative Parents

Substituents

Branched fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Branched fatty acids (LMFA01020077 )

Ontology

Physiological effect

Organoleptic effect

Taste

Sour

Odor

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0031221)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0031221)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031221)

Source

Endogenous

Endogenous (HMDB: HMDB0031221)

Animal

Animal (HMDB: HMDB0031221)

Exogenous

Food

Food (HMDB: HMDB0031221)

Exogenous (HMDB: HMDB0031221)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031221)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031221)

Lipid metabolism pathway (HMDB: HMDB0031221)

Cellular process

Cell signaling (HMDB: HMDB0031221)

Biochemical process

Lipid transport (HMDB: HMDB0031221)

Role

Biological role

Energy source (HMDB: HMDB0031221)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031221)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-15 °C	Not Available
Boiling Point	99.00 to 101.00 °C. @ 18.00 mm Hg	The Good Scents Company Information System
Water Solubility	18 mg/mL at 20 °C	Not Available
LogP	1.68	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	18.5 g/L	ALOGPS
logP	1.74	ALOGPS
logP	1.91	ChemAxon
logS	-0.8	ALOGPS
pKa (Strongest Acidic)	5.04	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.05 m³·mol⁻¹	ChemAxon
Polarizability	12.92 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]+	125.848	31661259
DarkChem	[M-H]-	121.896	31661259
DeepCCS	[M+H]+	132.527	30932474
DeepCCS	[M-H]-	129.752	30932474
DeepCCS	[M-2H]-	166.255	30932474
DeepCCS	[M+Na]+	140.892	30932474
AllCCS	[M+H]+	129.1	32859911
AllCCS	[M+H-H2O]+	124.8	32859911
AllCCS	[M+NH4]+	133.1	32859911
AllCCS	[M+Na]+	134.2	32859911
AllCCS	[M-H]-	127.8	32859911
AllCCS	[M+Na-2H]-	131.1	32859911
AllCCS	[M+HCOO]-	134.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.43 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9566 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.06 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	41.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1557.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	398.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	137.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	253.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	144.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	460.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	492.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	898.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	359.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1121.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	288.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	398.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	367.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	83.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Ethylbutanoic acid	CCC(CC)C(O)=O	1698.0	Standard polar	33892256
2-Ethylbutanoic acid	CCC(CC)C(O)=O	930.9	Standard non polar	33892256
2-Ethylbutanoic acid	CCC(CC)C(O)=O	958.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Ethylbutanoic acid,1TMS,isomer #1	CCC(CC)C(=O)O[Si](C)(C)C	1006.0	Semi standard non polar	33892256
2-Ethylbutanoic acid,1TBDMS,isomer #1	CCC(CC)C(=O)O[Si](C)(C)C(C)(C)C	1215.6	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-Ethylbutanoic acid EI-B (Non-derivatized)	splash10-007c-9000000000-dbe4308a7aba1f8b1fdf	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Ethylbutanoic acid EI-B (Non-derivatized)	splash10-007c-9000000000-dbe4308a7aba1f8b1fdf	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethylbutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00vl-9100000000-5476a8a41cb951ffee24	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethylbutanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9200000000-ef619e3db9bb76f469cf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethylbutanoic acid 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-Ethylbutanoic acid 10V, Positive-QTOF	splash10-014i-7900000000-d0f2c7acd46b28905b8e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylbutanoic acid 20V, Positive-QTOF	splash10-00di-9200000000-7d9fea82e813c2f83b15	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylbutanoic acid 40V, Positive-QTOF	splash10-0096-9000000000-af987f811e7a646f50c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylbutanoic acid 10V, Negative-QTOF	splash10-014i-4900000000-887e435df0b4ac88f541	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylbutanoic acid 20V, Negative-QTOF	splash10-00xr-9400000000-08331dd6d7c9cc7947c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylbutanoic acid 40V, Negative-QTOF	splash10-00xu-9000000000-d39604dbae21a94e0a18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylbutanoic acid 10V, Positive-QTOF	splash10-00xu-9200000000-46b98445339efcc97502	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylbutanoic acid 20V, Positive-QTOF	splash10-0006-9000000000-32c5d40205bdafeba3b8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylbutanoic acid 40V, Positive-QTOF	splash10-0006-9000000000-391959bd5ee3510956f4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylbutanoic acid 10V, Negative-QTOF	splash10-014i-0900000000-f02a8c6af96b787bcd37	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylbutanoic acid 20V, Negative-QTOF	splash10-014i-4900000000-ec5300d8498008e81096	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethylbutanoic acid 40V, Negative-QTOF	splash10-00or-9000000000-2c086168692290ae8df9	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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+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

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

FDB003245

KNApSAcK ID

Not Available

Chemspider ID

6649

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6915

PDB ID

Not Available

ChEBI ID

410868

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1021031

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Herrmann K: Effects of the anticonvulsant drug valproic acid and related substances on the early development of the zebrafish (Brachydanio rerio). Toxicol In Vitro. 1993 Jan;7(1):41-54. [PubMed:20732170 ]
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-Ethylbutanoic acid (HMDB0031221)

MOL for HMDB0031221 (2-Ethylbutanoic acid)

3D MOL for HMDB0031221 (2-Ethylbutanoic acid)

3D SDF for HMDB0031221 (2-Ethylbutanoic acid)

3D-SDF for HMDB0031221 (2-Ethylbutanoic acid)

PDB for HMDB0031221 (2-Ethylbutanoic acid)

3D PDB for HMDB0031221 (2-Ethylbutanoic acid)

SMILES for HMDB0031221 (2-Ethylbutanoic acid)

INCHI for HMDB0031221 (2-Ethylbutanoic acid)

Structure for HMDB0031221 (2-Ethylbutanoic acid)

3D Structure for HMDB0031221 (2-Ethylbutanoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra