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Bovine Metabolome Database



Showing metabocard for 2-Hydroxybutyric acid (BMDB00008)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-09-01 08:13:04
Accession Number BMDB00008
Common Name 2-Hydroxybutyric acid
Description 2-Hydroxybutyric acid is an organic acid that is involved in propanoate metabolism. It is produced in mammalian tissues (principaly hepatic) that catabolize L-threonine or synthesize glutathione. Oxidative stress or detoxification demands can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway forming methionine into the transsulfuration pathway forming cystathionine. 2-Hydroxybutyrate is released as a by-product when cystathionine is cleaved to cysteine that is incorporated into glutathione. 2-Hydroxybutyric acid is often found in the urine of patients suffering from lactic acidosis and ketoacidosis. 2-Hydroxybutyric acid generally appears at high concentrations in situations related to deficient energy metabolism (e.g., birth asphyxia) and also in inherited metabolic diseases affecting the central nervous system during neonatal development, such as "cerebral" lactic acidosis, glutaric aciduria type II, dihydrolipoyl dehydrogenase (E3) deficiency, and propionic acidemia. More recently it has been noted that elevated levels of alpha-hydroxybutyrate in the plasma is a good marker for insulin resistance and early stage type II diabetes (PMID: 19166731). It was concluded from studies done in the mid 1970's that an increased NADH2/NAD ratio was the most important factor for the production of 2-hydorxybutyric acid (PMID: 168632)
Synonyms
  1. (RS)-2-Hydroxybutyrate
  2. (RS)-2-Hydroxybutyric acid
  3. 2-Hydroxy-n-butyrate
  4. 2-Hydroxy-n-butyric acid
  5. 2-Hydroxybutanoate
  6. 2-Hydroxybutanoic acid
  7. 2-Hydroxybutyrate
  8. 2-hydroxy-Butanoate
  9. 2-hydroxy-Butanoic acid
  10. 2-hydroxy-DL-Butyrate
  11. 2-hydroxy-DL-Butyric acid
  12. DL-2-Hydroxybutanoate
  13. DL-2-Hydroxybutanoic acid
  14. DL-a-Hydroxybutyrate
  15. DL-a-Hydroxybutyric acid
  16. a-Hydroxy-n-butyrate
  17. a-Hydroxy-n-butyric acid
  18. a-Hydroxybutanoate
  19. a-Hydroxybutanoic acid
  20. a-Hydroxybutyrate
  21. a-Hydroxybutyric acid
  22. alpha-hydroxy-n-butyrate
  23. alpha-hydroxy-n-butyric acid
  24. DL-alpha-Hydroxybutyrate
  25. DL-alpha-Hydroxybutyric acid
  26. alpha-Hydroxybutanoate
  27. alpha-Hydroxybutanoic acid
  28. alpha-Hydroxybutyrate
  29. alpha-Hydroxybutyric acid
Chemical IUPAC Name 2-hydroxybutanoic acid
Chemical Formula C4H8O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Hydroxy Acids
Sub Class
  • Short chain hydroxy acids
Family
  • Mammalian_Metabolite
Species
  • secondary alcohol; carboxylic acid; alpha-hydroxyacid
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 104.104
Monoisotopic Molecular Weight 104.047340
Isomeric SMILES CCC(O)C(O)=O
Canonical SMILES CCC(O)C(O)=O
KEGG Compound ID C05984 Link Image
BioCyc ID CPD-3564 Link Image
BiGG ID 47130 Link Image
Wikipedia Link 2-Hydroxybutyric acid Link Image
METLIN ID 3783 Link Image
PubChem Compound 11266 Link Image
PubChem Substance 10347527 Link Image
ChEBI ID Not Available
CAS Registry Number 600-15-7
InChI Identifier InChI=1/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
Synthesis Reference Carlier, J. P.; Henry, C.; Lorin, V.; Rouffignat, K. Conversion of DL-threonine, D-threonine and 2-oxobutyrate into propionate and 2-hydroxybutyrate by Fusobacterium species. Letters in Applied Microbiology (1997), 25(5), 371-374.
Melting Point (Experimental) 44.2 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1000.0 mg/mL [MEYLAN,WM et al. (1996)]; 484.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.16 [Predicted by ALOGPS]; -0.2 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
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PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Propanoate Metabolism
HMDB Pathways
Name Propanoate Metabolism
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KEGG Pathways
Name Propanoate Metabolism
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SimCell Pathways
Name Propanoate Metabolism
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Graph
SBML
General References
  1. Wikipedia Link Image