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Bovine Rumen Metabolome Database



Showing metabocard for 3-Hydroxybutyric acid (RMDB00357)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-11 14:46:45
Accession Number RMDB00357
Common Name 3-Hydroxybutyric acid
Description 3-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 humans, 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)
Synonyms
  1. 3-OH-butyric acid
  2. 3-Hydroxybutanoate
  3. 3-Hydroxybutanoic acid
  4. 3-hydroxybutyric acid
  5. 3-Hydroxybutyrate
  6. DL-3-Hydroxybutyrate
  7. DL-3-Hydroxybutyric acid
  8. b-Hydroxy-n-butyrate
  9. b-Hydroxy-n-butyric acid
  10. b-Hydroxybutanoate
  11. b-Hydroxybutanoic acid
  12. b-Hydroxybutyrate
  13. b-Hydroxybutyric acid
  14. beta-Hydroxy-n-butyrate
  15. beta-Hydroxy-n-butyric acid
  16. beta-Hydroxybutyrate
  17. beta-Hydroxybutyric acid
  18. beta-Hydroxybutanoate
  19. beta-Hydroxybutanoic acid
  20. Biopol
  21. 3-hydroxy-butanoic acid
  22. 3-hydroxy-butanoate
  23. 3-hydroxy-butyric acid
  24. 3-hydroxy-butyrate
  25. beta-Hydroxybuttersaeure
  26. DL-b-Hydroxybutyric acid
  27. DL-beta-Hydroxybutyric acid
Chemical IUPAC Name 3-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
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 104.104
Monoisotopic Molecular Weight 104.047340
Isomeric SMILES CC(O)CC(O)=O
Canonical SMILES CC(O)CC(O)=O
KEGG Compound ID C01089 Link Image
BioCyc ID CPD-335 Link Image
BiGG ID Not Available
Wikipedia Link 3-Hydroxybutyric acid Link Image
METLIN ID 125 Link Image
PubChem Compound 441 Link Image
PubChem Substance 2380 Link Image
ChEBI ID 20067 Link Image
CAS Registry Number 300-85-6
InChI Identifier InChI=1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
Synthesis Reference Yang, 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.
Melting Point (Experimental) 46 oC
Experimental Water Solubility 444 mg/mL [HMP experimental] Source: PhysProp
Predicted Water Solubility 539.0 mg/mL [Predicted by ALOGPS]; 1000 mg/mL at 25 oC [MEYLAN,WM et al. (1996)] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.50 [Predicted by ALOGPS]; -0.5 [Predicted by PubChem via XLOGP]; -0.47 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location
  • Cow_Milk
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 63.29 +/- 12.55 uM
Age 4-5 years old
Sex Female (lactating)
Condition Normal (0% barley grain in dry matter (DM) basis)
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 52.7 +/- 11.2 uM
Age N/A
Sex Female
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Burim N. Ametaj, Qendrim Zebeli, Fozia Saleem, Nikolaos Psychogios, Michael J. Lewis, Suzanna M. Dunn, Jianguo Xia and David S. Wishart Metabolomics 2010;6(4):583-594
Concentrations (Abnormal)
Biofluid Rumen
Value 77 +/- 13 uM
Age 4-5 years old
Sex Female (lactating)
Condition 15% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 90 +/- 23 uM
Age 4-5 years old
Sex Female (lactating)
Condition 30% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 110 +/- 40 uM
Age 4-5 years old
Sex Female (lactating)
Condition 45% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image