Isovaleric acid (ECMDB00718) (M2MDB000177)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)Transporters (1)XML
Proteins (3)
Record Information
Version2.0
Creation Date2012-05-31 13:00:42 -0600
Update Date2015-09-13 15:15:19 -0600
Secondary Accession Numbers
  • ECMDB00718
Identification
Name:Isovaleric acid
DescriptionIsovaleric acid, is a natural short-chain fatty acid. It is clear colorless liquid that is sparingly soluble in water, but extremely soluble in most common organic solvents.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 3-Methyl-N-butyrate
  • 3-Methyl-N-butyric acid
  • 3-Methylbutanoate
  • 3-Methylbutanoic acid
  • 3-Methylbutyrate
  • 3-Methylbutyrate: isopropyl-acetate
  • 3-Methylbutyrate: isopropyl-Acetic acid
  • 3-Methylbutyric acid
  • 3-Methylbutyric acid: isopropyl-Acetate
  • 3-Methylbutyric acid: isopropyl-Acetic acid
  • B-Methylbutyrate
  • B-Methylbutyric acid
  • Beta-Methylbutyrate
  • Beta-Methylbutyric acid
  • Delphinate
  • Delphinic acid
  • Isopentanoate
  • Isopentanoic acid
  • Isopropylacetate
  • Isopropylacetic acid
  • Isovalerate
  • Isovalerianate
  • Isovalerianic acid
  • Isovaleric acid
  • β-Methylbutyrate
  • β-Methylbutyric acid
Chemical Formula:C5H10O2
Weight:Average: 102.1317
Monoisotopic: 102.068079564
InChI Key:GWYFCOCPABKNJV-UHFFFAOYSA-N
InChI:InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
CAS number:503-74-2
IUPAC Name:3-methylbutanoic acid
Traditional IUPAC Name:isovaleric acid
SMILES:CC(C)CC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:-1
Melting point:-29.3 °C
Experimental Properties:
PropertyValueSource
Water Solubility:40.7 mg/ml [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:1.039PhysProp
Predicted Properties
PropertyValueSource
Water Solubility64.9 g/LALOGPS
logP1.26ALOGPS
logP1.21ChemAxon
logS-0.2ALOGPS
pKa (Strongest Acidic)5.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.42 m³·mol⁻¹ChemAxon
Polarizability10.99 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Isovaleric acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Valine + L-Valine
(R)-2,3-Dihydroxy-isovalerate > Water + Isovaleric acid
SMPDB Pathways:
Valine BiosynthesisPW000812 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-9e19eb5f5137b78591dfView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-43967f1315b6b575f330View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-9e19eb5f5137b78591dfView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-43967f1315b6b575f330View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-2825512cee017b3ab87cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-059f-9200000000-628e11f1ffbaa913ef57View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0gvo-9300000000-16b5d15d26810b72bb36View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-692791435c37fa74a692View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b4c1b59653cd4d803637View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-03dl-9000000000-b0f7e399edb7f95572edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03dl-9000000000-c8be68873f336c8de6d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-d0f20bc9813dcba79e8bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-63b09019c280c88ee64dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-1900000000-ef9ee29c1febd59e6a00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-d0f20bc9813dcba79e8bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-63b09019c280c88ee64dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1900000000-ef9ee29c1febd59e6a00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-871b21c20bba686fb915View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-6ce72c7a41bfb4bc1b2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0nmi-9300000000-efcb74e7796ba9769f97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-e825f0aa9ab54c1695d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-9ba126f982634fdc9406View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-afb863a56c8763c30251View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-8900000000-244535e4070d536a29b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-9300000000-93ed2bc326380cb0d880View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-44b2fa11a5a6daab8dd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9000000000-f59a47a684453302cbedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-83176e54a19e36af76f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-81052c8b00621fcf0443View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-4c159e60dacc58e6ba98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-7900000000-fd28737d49ed09628cfaView in MoNA
MSMass Spectrum (Electron Ionization)splash10-03dl-9000000000-e7c77b2bc7f3ac5191e9View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Ackman RG: Birthweights in the Faroe Islands: possible role of isovaleric acid. J Intern Med. 1989 Feb;225(2):73-5. Pubmed: 2646392
  • Ara K, Hama M, Akiba S, Koike K, Okisaka K, Hagura T, Kamiya T, Tomita F: Foot odor due to microbial metabolism and its control. Can J Microbiol. 2006 Apr;52(4):357-64. Pubmed: 16699586
  • Arthur K, Hommes FA: Simple isotope dilution assay for propionic acid and isovaleric acid. J Chromatogr B Biomed Appl. 1995 Nov 3;673(1):132-5. Pubmed: 8925066
  • Hoffmann GF, von Kries R, Klose D, Lindner M, Schulze A, Muntau AC, Roschinger W, Liebl B, Mayatepek E, Roscher AA: Frequencies of inherited organic acidurias and disorders of mitochondrial fatty acid transport and oxidation in Germany. Eur J Pediatr. 2004 Feb;163(2):76-80. Epub 2004 Jan 9. Pubmed: 14714182
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Silva MF, Selhorst J, Overmars H, van Gennip AH, Maya M, Wanders RJ, de Almeida IT, Duran M: Characterization of plasma acylcarnitines in patients under valproate monotherapy using ESI-MS/MS. Clin Biochem. 2001 Nov;34(8):635-8. Pubmed: 11849623
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Imada, Yukio; Mizuno, Sumiko; Mikawa, Takashi. Manufacture of isovaleric acid and 2-methylbutyric acid. Jpn. Kokai Tokkyo Koho (1986), 3 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID28484
HMDB IDHMDB00718
Pubchem Compound ID10430
Kegg IDC08262
ChemSpider ID10001
WikipediaIsovaleric_acid
BioCyc IDNot Available
Ligand ExpoIVA

Enzymes

Protein Details
1. Dihydroxy-acid dehydratase
General function:
Involved in metabolic process
Specific function:
2,3-dihydroxy-3-methylbutanoate = 3-methyl-2- oxobutanoate + H(2)O
Gene Name:
ilvD
Uniprot ID:
P05791
Molecular weight:
65531
Reactions
2,3-dihydroxy-3-methylbutanoate = 3-methyl-2-oxobutanoate + H(2)O.
Protein Details
2. Branched-chain-amino-acid aminotransferase
General function:
Involved in catalytic activity
Specific function:
Acts on leucine, isoleucine and valine
Gene Name:
ilvE
Uniprot ID:
P0AB80
Molecular weight:
34093
Reactions
L-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + L-glutamate.
L-isoleucine + 2-oxoglutarate = (S)-3-methyl-2-oxopentanoate + L-glutamate.
L-valine + 2-oxoglutarate = 3-methyl-2-oxobutanoate + L-glutamate.

Transporters

Protein Details
1. Short-chain fatty acids transporter
General function:
Lipid transport and metabolism
Specific function:
Responsible for the intake of short-chain fatty acids
Gene Name:
atoE
Uniprot ID:
P76460
Molecular weight:
47527