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Showing metabocard for 3-Hydroxybutyric acid (BMDB0000357)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:29:14 UTC
Update Date2020-06-04 20:35:41 UTC
MCDB ID BMDB0000357
Secondary Accession Numbers
  • BMDB00357
Metabolite Identification
Common Name3-Hydroxybutyric acid
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 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 3-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 3-Hydroxybutyric acid is a potentially toxic compound. 3-Hydroxybutyric acid has been found to be associated with several diseases known as pyruvate dehydrogenase phosphatase deficiency, schizophrenia, adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency, and colorectal cancer; also 3-hydroxybutyric acid has been linked to the inborn metabolic disorders including medium chain acyl-coa dehydrogenase deficiency.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point46 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility444 mg/mLNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-92be5c49a099fe1d98652014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-01ot-1920000000-c93138bf9d35643fef302014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-8900000000-e632e14fb4be28bdb7862014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014l-1900000000-e192caba63f0340406242014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-92be5c49a099fe1d98652017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01ot-1920000000-c93138bf9d35643fef302017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-8900000000-e632e14fb4be28bdb7862017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014l-1900000000-e192caba63f0340406242017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-d06c5ac1a3733a38ea052017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9000000000-63f261a4dc876e2642462016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ei-9710000000-2652bd46b41e50defdb02017-10-06View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9200000000-4156904e7472b5e972492012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1e2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d7944402012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0zfr-4900000000-537084557f5986f16b312012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-4900000000-537084557f5986f16b312017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-9000000000-7f0ec480b3c3c3911acd2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9100000000-05c4623b015ff4300a6d2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-9000000000-cbe0653845ffe4dc6ad42016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-e55d47308c7464e4cb222016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-8900000000-06dfbf939f6d19983ebe2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9200000000-48b6e9b8656d41bff9cf2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-f7d61596ff4428fe6b092016-09-12View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0007-9000000000-7fc414806153ebd8822c2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified69 +/- 7 uM details
Detected and Quantified110 +/- 20 uM details
Detected and Quantified10 - 631 uM details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected and Quantified10 - 531 uM details
Detected and Quantified12 - 121 uM details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected and Quantified26 +/- 3 uM details
Detected and Quantified29 +/- 2 uM details
Detected and Quantified26 +/- 5 uM details
Detected and Quantified30 +/- 3 uM details
Detected and Quantified28 +/- 2.92 uM details
Detected and Quantified24 +/- 5 uM details
Detected and Quantified34 +/- 11 uM details
HMDB IDHMDB0000357
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021797
KNApSAcK IDNot Available
Chemspider ID428
KEGG Compound IDC01089
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-hydroxybutyrate
METLIN ID125
PubChem Compound441
PDB IDNot Available
ChEBI ID20067
References
Synthesis ReferenceYang, Wenling; Ma, Peisheng; Wang, Jianing; Wang, Chunfang; Li, Haixia. Study on the process of chemical synthesis of 3-hydroxybutyric acid. Huaxue Gongcheng (Xi'an, China) (2002), 30(5), 74-78.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0. [PubMed:11286410 ]
  2. Nielsen NI, Ingvartsen KL, Larsen T: Diurnal variation and the effect of feed restriction on plasma and milk metabolites in TMR-fed dairy cows. J Vet Med A Physiol Pathol Clin Med. 2003 Mar;50(2):88-97. [PubMed:12667199 ]
  3. Larsen T, Nielsen NI: Fluorometric determination of beta-hydroxybutyrate in milk and blood plasma. J Dairy Sci. 2005 Jun;88(6):2004-9. doi: 10.3168/jds.S0022-0302(05)72876-9. [PubMed:15905430 ]
  4. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  5. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
  6. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  7. Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
  8. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
  9. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
  10. Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]
  11. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  12. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  13. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.