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Record Information
Version1.0
Creation Date2016-07-13 19:43:19 UTC
Update Date2021-04-30 20:57:57 UTC
LmdbLMDB00144
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxybutyric acid
Description3-Hydroxybutyric acid (or beta-hydroxybutyrate) is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-hydroxybutyrate in blood and urine are raised in ketosis. In animals, 3-hydroxybutyrate is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low. Blood levels of 3-Hydroxybutyric acid levels may be monitored in diabetic patients to look for diabetic ketoacidosis. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing mammals. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate (AcAc) and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first 2 weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies is utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life. (PMID 3884391 ).
Structure
Thumb
Synonyms
ValueSource
(1)-3-Hydroxybutyric acidChEBI
3 HBAChEBI
3-HydroxybuttersaeureChEBI
3-OH-Butyric acidChEBI
beta-Hydroxy-N-butyric acidChEBI
beta-Hydroxybutanoic acidChEBI
beta-HydroxybuttersaeureChEBI
beta-Hydroxybutyric acidChEBI
BHBAChEBI
DL-beta-Hydroxybutyric acidChEBI
(1)-3-HydroxybutyrateGenerator
3-OH-ButyrateGenerator
b-Hydroxy-N-butyrateGenerator
b-Hydroxy-N-butyric acidGenerator
beta-Hydroxy-N-butyrateGenerator
Β-hydroxy-N-butyrateGenerator
Β-hydroxy-N-butyric acidGenerator
b-HydroxybutanoateGenerator
b-Hydroxybutanoic acidGenerator
beta-HydroxybutanoateGenerator
Β-hydroxybutanoateGenerator
Β-hydroxybutanoic acidGenerator
b-HydroxybuttersaeureGenerator
Β-hydroxybuttersaeureGenerator
b-HydroxybutyrateGenerator
b-Hydroxybutyric acidGenerator
beta-HydroxybutyrateGenerator
Β-hydroxybutyrateGenerator
Β-hydroxybutyric acidGenerator
DL-b-HydroxybutyrateGenerator
DL-b-Hydroxybutyric acidGenerator
DL-beta-HydroxybutyrateGenerator
DL-Β-hydroxybutyrateGenerator
DL-Β-hydroxybutyric acidGenerator
3-HydroxybutyrateGenerator
3-Hydroxy-butanoateHMDB
3-Hydroxy-butanoic acidHMDB
3-Hydroxy-butyrateHMDB
3-Hydroxy-butyric acidHMDB
3-HydroxybutanoateHMDB
3-Hydroxybutanoic acidHMDB
BiopolHMDB
DL-3-HydroxybutyrateHMDB
DL-3-Hydroxybutyric acidHMDB
beta Hydroxybutyric acidHMDB
3 Hydroxybutyric acidHMDB
beta HydroxybutyrateHMDB
(+ -)-3-Hydroxybutyric acidHMDB
3 HydroxybutyrateHMDB
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name3-hydroxybutanoic acid
Traditional Name3 hydroxybutyrate
CAS Registry Number300-85-6
SMILES
CC(O)CC(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
InChI KeyWHBMMWSBFZVSSR-UHFFFAOYSA-N
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-92be5c49a099fe1d9865Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-01ot-1920000000-c93138bf9d35643fef30Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-8900000000-e632e14fb4be28bdb786Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014l-1900000000-e192caba63f034040624Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-92be5c49a099fe1d9865Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01ot-1920000000-c93138bf9d35643fef30Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-8900000000-e632e14fb4be28bdb786Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014l-1900000000-e192caba63f034040624Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-d06c5ac1a3733a38ea05Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9000000000-63f261a4dc876e264246Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ei-9710000000-2652bd46b41e50defdb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9200000000-4156904e7472b5e97249Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d794440Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0zfr-4900000000-537084557f5986f16b31Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-4900000000-537084557f5986f16b31Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-9000000000-7f0ec480b3c3c3911acdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9100000000-05c4623b015ff4300a6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-9000000000-cbe0653845ffe4dc6ad4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-e55d47308c7464e4cb22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-8900000000-06dfbf939f6d19983ebeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9200000000-48b6e9b8656d41bff9cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-f7d61596ff4428fe6b09Spectrum
MSMass Spectrum (Electron Ionization)splash10-0007-9000000000-7fc414806153ebd8822cSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Colostrum
  • Kidney perfusate
  • Meat
  • Milk
  • Plasma
  • Ruminal Fluid
  • Serum
  • Synovial Fluid
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • S. F. Graham, T. ...
details
Kidney perfusateDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified0.86+/-0.18 umol/gNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified0.94+/-0.26 umol/gNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified1.26+/-0.42 umol/gNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified1.47+/-0.39 umol/gNot AvailableBovine
    • S. F. Graham, T. ...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified12-121 uMNot AvailableBovine details
MilkDetected and Quantified10-531 uMNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableEquine details
PlasmaDetected and Quantified2970 +/- 784 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected and Quantified4547 +/- 1058 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected and Quantified8042 +/- 1256 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected and Quantified1550 +/- 170 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Trabi M, Keller M...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
PlasmaDetected and Quantified500 +/- 30 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected and Quantified640 +/- 90 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
Ruminal FluidDetected and Quantified131 +/- 8.0 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified76.5 +/- 17 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified80.1 +/- 9.4 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified110 +/- 40 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified53 +/- 12 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified63 +/- 13 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified63 +/- 13 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified77 +/- 13 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified90 +/- 23 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified606.3 +/- 14 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified63.3 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified78.6 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified89.4 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified109.9 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified44.8 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified46.7 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified60.6 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified77.1 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected and Quantified553.7811 +/- 209.1351 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailableOvine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableOvine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
SerumDetected and Quantified631.5763 +/- 313.5592 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified596.9241 +/- 169.5479 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified161.92 +/- 54.25 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified353.1989 +/- 176.1426 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified543.6782 +/- 157.9971 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified400.0996 +/- 123.3543 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified375.1492 +/- 203.0711 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified411.6994 +/- 128.4455 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified532.6358 +/- 197.8191 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified389.7844 +/- 116.8778 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified573.6844 +/- 247.6773 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified402.9691 +/- 108.4581 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified676.5352 +/- 396.5541 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified412.8304 +/- 110.7007 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified339.8844 +/- 167.5501 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified568.025 +/- 226.7049 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified417.7539 +/- 123.8176 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified672.3698 +/- 331.2823 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified391.6459 +/- 137.4591 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified376.2224 +/- 171.489 uM
Normal
Ovine
    • Goldansaz et al.,...
details
Synovial FluidDetected but not QuantifiedNot ApplicableNot AvailableOvine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableOvine details
DrugBank IDNot Available
HMDB IDHMDB0000357
FooDB IDFDB021797
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID125
PDB IDNot Available
Wikipedia Link3-hydroxybutyrate
Chemspider ID428
ChEBI ID20067
PubChem Compound ID441
Kegg Compound IDC01089
YMDB IDYMDB01561
ECMDB IDECMDB21418
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yeh YY, Sheehan PM: Preferential utilization of ketone bodies in the brain and lung of newborn rats. Fed Proc. 1985 Apr;44(7):2352-8. [3884391 ]