You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB01606
Name3-Methylbutanoic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description3-Methylbutanoic acid (isovaleric acid) is a natural fatty acid found in a wide variety of plants and essential oils. It has a strong pungent cheesy or sweaty smell, but its volatile esters have pleasing scents and are used widely in perfumery. Isovaleric acid is what gives stale hops its characteristically cheesy aroma and flavor. It has been suggested that isovaleric acid may be the dominant odorant in some high-Brettanomyces wines. [PMID: 17850808]
Structure
Thumb
Synonyms
  • 3-Methyl-n-butyrate
  • 3-Methyl-n-butyric acid
  • 3-Methylbutanoate
  • 3-Methylbutanoic acid
  • 3-methylbutanoic acid (isovaleric acid)
  • 3-Methylbuttersaeure
  • 3-Methylbutyrate
  • 3-Methylbutyric acid
  • Acetic acid, isopropyl-
  • b-Methylbutyrate
  • b-Methylbutyric acid
  • beta-Methylbutyrate
  • beta-Methylbutyric acid
  • Butanoic acid, 3-methyl-
  • Butyric acid, 3-methyl-
  • Delphinate
  • Delphinic acid
  • iso-C4H9COOH
  • isobutylformic acid
  • Isopentanoate
  • Isopentanoic acid
  • Isopropylacetate
  • Isopropylacetic acid
  • Isovalerate
  • Isovalerianate
  • Isovalerianic
  • Isovalerianic acid
  • Isovaleriansaeure
  • Isovaleric acid
  • Isovaleric acid sodium salt
  • Kyselina isovalerova
  • Methylbutanoic acid
  • Β-methylbutyrate
  • Β-methylbutyric acid
  • Isobutylformate
  • 3-Methyl butyric acid
  • 3-Methylbutyric acid: isopropyl-acetate
  • 3-Methylbutyric acid: isopropyl-acetic acid
  • 3-Methyl-1-butanoic acid
CAS number503-74-2
WeightAverage: 102.1317
Monoisotopic: 102.068079564
InChI KeyGWYFCOCPABKNJV-UHFFFAOYSA-N
InChIInChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
IUPAC Name3-methylbutanoic acid
Traditional IUPAC Nameisovaleric acid
Chemical FormulaC5H10O2
SMILESCC(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
StateLiquid
Charge0
Melting point-29.3 °C
Experimental Properties
PropertyValueReference
Water Solubility40.7 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP1.16 [HANSCH,C ET AL. (1995)]PhysProp
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 LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
AcidFDB001324
AnimalFDB001324
CheeseFDB001324
FeetFDB001324
RancidFDB001324
SourFDB001324
StinkyFDB001324
SweatFDB001324
SweatyFDB001324
TropicalFDB001324
SMPDB Pathways
Valine BiosynthesisPW002474 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
3-Methylbutanoic acid + L-Glutamic acidOxoglutaric acid + L-Valine
(R)-2,3-Dihydroxy-isovaleratewater + 3-Methylbutanoic acid
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-9e19eb5f5137b78591dfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-43967f1315b6b575f330JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-9e19eb5f5137b78591dfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-43967f1315b6b575f330JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-2825512cee017b3ab87cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-059f-9200000000-628e11f1ffbaa913ef57JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0gvo-9300000000-16b5d15d26810b72bb36JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-692791435c37fa74a692JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b4c1b59653cd4d803637JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-03dl-9000000000-b0f7e399edb7f95572edJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03dl-9000000000-c8be68873f336c8de6d6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-d0f20bc9813dcba79e8bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-63b09019c280c88ee64dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-1900000000-ef9ee29c1febd59e6a00JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-d0f20bc9813dcba79e8bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-63b09019c280c88ee64dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1900000000-ef9ee29c1febd59e6a00JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-e825f0aa9ab54c1695d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-9ba126f982634fdc9406JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-afb863a56c8763c30251JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-8900000000-244535e4070d536a29b3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-9300000000-93ed2bc326380cb0d880JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-44b2fa11a5a6daab8dd0JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-03dl-9000000000-e7c77b2bc7f3ac5191e9JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Dickinson, J. R., Lanterman, M. M., Danner, D. J., Pearson, B. M., Sanz, P., Harrison, S. J., Hewlins, M. J. (1997). "A 13C nuclear magnetic resonance investigation of the metabolism of leucine to isoamyl alcohol in Saccharomyces cerevisiae." J Biol Chem 272:26871-26878.9341119
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28484
HMDB IDHMDB00718
Pubchem Compound ID8314
Kegg IDC08262
ChemSpider ID10001
FOODB IDFDB001324
Wikipedia ID3-Methylbutanoic acid
BioCyc IDNot Available

Enzymes

General function:
Involved in metabolic process
Specific function:
2,3-dihydroxy-3-methylbutanoate = 3-methyl-2- oxobutanoate + H(2)O
Gene Name:
ILV3
Uniprot ID:
P39522
Molecular weight:
62860.60156
Reactions
2,3-dihydroxy-3-methylbutanoate → 3-methyl-2-oxobutanoate + H(2)O.