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3-Hydroxybutyric acid (YMDB01561)

Identification
YMDB IDYMDB01561
Name3-Hydroxybutyric acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description3-Hydroxybutyric acid, also known as 3-hydroxybutyrate or 3-hydroxybuttersaeure, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. 3-Hydroxybutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 3-Hydroxybutyric acid is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • 3-Hydroxybutyrate
  • beta-hydroxybutyrate
  • beta-hydroxybutyric acid
  • (1)-3-Hydroxybutyric acid
  • 3 HBA
  • 3-Hydroxybuttersaeure
  • 3-OH-Butyric acid
  • beta-Hydroxy-N-butyric acid
  • beta-Hydroxybutanoic acid
  • beta-Hydroxybuttersaeure
  • BHBA
  • DL-beta-Hydroxybutyric acid
  • (1)-3-Hydroxybutyrate
  • 3-OH-Butyrate
  • b-Hydroxy-N-butyrate
  • b-Hydroxy-N-butyric acid
  • beta-Hydroxy-N-butyrate
  • Β-hydroxy-N-butyrate
  • Β-hydroxy-N-butyric acid
  • b-Hydroxybutanoate
  • b-Hydroxybutanoic acid
  • beta-Hydroxybutanoate
  • Β-hydroxybutanoate
  • Β-hydroxybutanoic acid
  • b-Hydroxybuttersaeure
  • Β-hydroxybuttersaeure
  • b-Hydroxybutyrate
  • b-Hydroxybutyric acid
  • Β-hydroxybutyrate
  • Β-hydroxybutyric acid
  • DL-b-Hydroxybutyrate
  • DL-b-Hydroxybutyric acid
  • DL-beta-Hydroxybutyrate
  • DL-Β-hydroxybutyrate
  • DL-Β-hydroxybutyric acid
  • 3-Hydroxy-butanoate
  • 3-Hydroxy-butanoic acid
  • 3-Hydroxy-butyrate
  • 3-Hydroxy-butyric acid
  • 3-Hydroxybutanoate
  • 3-Hydroxybutanoic acid
  • Biopol
  • DL-3-Hydroxybutyrate
  • DL-3-Hydroxybutyric acid
  • beta Hydroxybutyric acid
  • 3 Hydroxybutyric acid
  • beta Hydroxybutyrate
  • (+ -)-3-Hydroxybutyric acid
  • 3 Hydroxybutyrate
CAS number300-85-6
WeightAverage: 104.1045
Monoisotopic: 104.047344122
InChI KeyWHBMMWSBFZVSSR-UHFFFAOYSA-N
InChIInChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
IUPAC Name3-hydroxybutanoic acid
Traditional IUPAC Name3 hydroxybutyrate
Chemical FormulaC4H8O3
SMILESCC(O)CC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point46 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility539 g/LALOGPS
logP-0.5ALOGPS
logP-0.39ChemAxon
logS0.71ALOGPS
pKa (Strongest Acidic)4.41ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.46 m³·mol⁻¹ChemAxon
Polarizability10.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Fatty acid biosynthesisPW002458 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid biosynthesisec00061 Map00061
SMPDB Reactions
Acetoacetic acid → 3-Hydroxybutyric acid
3-Hydroxybutyric acid → But-2-enoic acid
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
600 ± 30 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-92be5c49a099fe1d9865JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-01ot-1920000000-c93138bf9d35643fef30JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-8900000000-e632e14fb4be28bdb786JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014l-1900000000-e192caba63f034040624JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-92be5c49a099fe1d9865JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01ot-1920000000-c93138bf9d35643fef30JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-8900000000-e632e14fb4be28bdb786JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014l-1900000000-e192caba63f034040624JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-d06c5ac1a3733a38ea05JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9000000000-63f261a4dc876e264246JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ei-9710000000-2652bd46b41e50defdb0JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9200000000-4156904e7472b5e97249JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d794440JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0zfr-4900000000-537084557f5986f16b31JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-4900000000-537084557f5986f16b31JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-9000000000-7f0ec480b3c3c3911acdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9100000000-05c4623b015ff4300a6dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-9000000000-cbe0653845ffe4dc6ad4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-e55d47308c7464e4cb22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-8900000000-06dfbf939f6d19983ebeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9200000000-48b6e9b8656d41bff9cfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-f7d61596ff4428fe6b09JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0007-9000000000-7fc414806153ebd8822cJSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID20067
HMDB IDHMDB00357
Pubchem Compound ID441
Kegg IDC01089
ChemSpider ID428
FOODB IDFDB021797
Wikipedia ID3-hydroxybutyrate
BioCyc IDCPD-335