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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-04-19 22:20:42 UTC
HMDB IDHMDB00011
Secondary Accession NumbersNone
Metabolite Identification
Common Name(R)-3-Hydroxybutyric acid
Description(R)-3-Hydroxybutyric acid is a butyric acid substituted with a hydroxyl group in the beta or 3 position. 3-hydroxybutyric acid, or beta-hydroxybutyrate, is involved in the synthesis and degradation of ketone bodies. Like the other ketone bodies (acetoacetate and acetone), levels of beta-hydroxybutyrate are raised in the blood and urine in ketosis. Beta-hydroxybutyrate is a typical partial-degradation product of branched-chain amino acids (primarily valine) released from muscle for hepatic and renal gluconeogenesis This acid is metabolized by 3-hydroxybutyrate dehydrogenase (catalyzes the oxidation of D-3-hydroxybutyrate to form acetoacetate, using NAD+ as an electron acceptor). The enzyme functions in nervous tissues and muscles, enabling the use of circulating hydroxybutyrate as a fuel. In the liver mitochondrial matrix, the enzyme can also catalyze the reverse reaction, a step in ketogenesis. 3-Hydroxybutyric acid is a chiral compound having two enantiomers, D-3-hydroxybutyric acid and L-3-hydroxybutyric acid. In humans, beta-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. It can also be used for the synthesis of biodegradable plastics (Wikipedia).
Structure
Thumb
Synonyms
  1. (R)-(-)-b-Hydroxybutyrate
  2. (R)-(-)-b-Hydroxybutyric acid
  3. (R)-(-)-beta-Hydroxybutyrate
  4. (R)-(-)-beta-Hydroxybutyric acid
  5. (R)-3-Hydroxybutanoate
  6. (R)-3-Hydroxybutanoic acid
  7. (R)-3-Hydroxybutyrate
  8. 3-D-Hydroxybutyrate
  9. 3-D-Hydroxybutyric acid
  10. 3-delta-Hydroxybutyrate
  11. 3-delta-Hydroxybutyric acid
  12. BHIB
  13. D-(-)-3-Hydroxybutyrate
  14. D-3-Hydroxybutyrate
  15. D-3-Hydroxybutyric acid
  16. D-beta-Hydroxybutyrate
  17. delta-(-)-3-Hydroxybutyrate
  18. delta-3-Hydroxybutyrate
  19. delta-3-Hydroxybutyric acid
  20. delta-beta-Hydroxybutyrate
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name(3R)-3-hydroxybutanoic acid
Traditional Name(-)-3-hydroxybutyric acid
CAS Registry Number625-72-9
SMILES
C[C@@H](O)CC(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1
InChI KeyWHBMMWSBFZVSSR-GSVOUGTGSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassHydroxy Acids and Derivatives
Sub ClassBeta Hydroxy Acids and Derivatives
Other Descriptors
  • 3-hydroxy monocarboxylic acid(ChEBI)
  • Aliphatic Acyclic Compounds
  • Hydroxy fatty acids(Lipidmaps)
  • Organic Compounds
  • Straight Chain Fatty Acids
  • hydroxy fatty acid(ChEBI)
  • hydroxybutyric acid(ChEBI)
  • short-chain fatty acid(ChEBI)
  • straight-chain saturated fatty acid(ChEBI)
Substituents
  • Carboxylic Acid
  • Secondary Alcohol
  • Short Chain Hydroxy Acid
Direct ParentBeta Hydroxy Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Butanoate metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point49 - 50 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 Area57.53ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.46ChemAxon
Polarizability9.96ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Ketone Body MetabolismSMP00071map00072
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified36 +/- 20 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified86 +/- 53 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified38 +/- 31 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified286 (207-365) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.4 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified48.0 (0.00-200.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.6 (1.3-6.4) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1500.0 +/- 100.0 uMChildren (1-13 years old)Both
Diabetes
details
BloodDetected and Quantified7700.0 +/- 300.0 uMChildren (1-13 years old)Both
Diabetes
details
BloodDetected and Quantified1400.0 +/- 100.0 uMAdult (>18 years old)Both
Diabetes
details
BloodDetected and Quantified7700.0 +/- 200.0 uMAdult (>18 years old)Both
Diabetes
details
Cerebrospinal Fluid (CSF)Detected and Quantified430 (359-501) uMAdult (>18 years old)Both
Meningitis
details
Cerebrospinal Fluid (CSF)Detected and Quantified6360 (5350-7370) uMAdult (>18 years old)Both
Diabetes
details
UrineDetected and Quantified224 umol/mmol creatinineAdult (>18 years old)BothDiabetes details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. Sheikh-Ali M, Karon BS, Basu A, Kudva YC, Muller LA, Xu J, Schwenk WF, Miles JM: Can serum beta-hydroxybutyrate be used to diagnose diabetic ketoacidosis? Diabetes Care. 2008 Apr;31(4):643-7. Epub 2008 Jan 9. Pubmed: 18184896
  2. Tasker RC, Lutman D, Peters MJ: Hyperventilation in severe diabetic ketoacidosis. Pediatr Crit Care Med. 2005 Jul;6(4):405-11. Pubmed: 15982426
  3. Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. Pubmed: 6321058
Meningitis
  1. Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. Pubmed: 15627241
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021869
KNApSAcK IDNot Available
Chemspider ID83181
KEGG Compound IDC01089
BioCyc IDCPD-335
BiGG ID36784
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00011
Metagene LinkHMDB00011
METLIN IDNot Available
PubChem Compound92135
PDB ID3HR
ChEBI ID17066
References
Synthesis ReferenceLe Sann, Christine; Munoz, Dulce M.; Saunders, Natalie; Simpson, Thomas J.; Smith, David I.; Soulas, Florilene; Watts, Paul; Willis, Christine L. Assembly intermediates in polyketide biosynthesis: enantioselective syntheses of b-hydroxycarbonyl compounds
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Pan JW, Rothman TL, Behar KL, Stein DT, Hetherington HP: Human brain beta-hydroxybutyrate and lactate increase in fasting-induced ketosis. J Cereb Blood Flow Metab. 2000 Oct;20(10):1502-7. Pubmed: 11043913
  2. Pan JW, Telang FW, Lee JH, de Graaf RA, Rothman DL, Stein DT, Hetherington HP: Measurement of beta-hydroxybutyrate in acute hyperketonemia in human brain. J Neurochem. 2001 Nov;79(3):539-44. Pubmed: 11701757
  3. Plecko B, Stoeckler-Ipsiroglu S, Schober E, Harrer G, Mlynarik V, Gruber S, Moser E, Moeslinger D, Silgoner H, Ipsiroglu O: Oral beta-hydroxybutyrate supplementation in two patients with hyperinsulinemic hypoglycemia: monitoring of beta-hydroxybutyrate levels in blood and cerebrospinal fluid, and in the brain by in vivo magnetic resonance spectroscopy. Pediatr Res. 2002 Aug;52(2):301-6. Pubmed: 12149510
  4. Raunio RP, Leivo PV, Kuusinen AM: Bioluminescent assay of D-3-hydroxybutyrate in serum. J Biolumin Chemilumin. 1986 Jun;1(1):11-4. Pubmed: 3503522
  5. Bernardi, R. et al., Chem. Commun., 1984, 460, (resoln)
  6. Encyclopedia of Food and Color Additives, (ed. Burdock, G.A.), CRC Press, 1997, 994-995, (Et ester)
  7. Fenaroli's Handbook of Flavor Ingredients, 3rd edn., (ed. Burdock, G.A.), CRC Press, 1995, 1, 238, (Et ester)
  8. Forsyth, W.G.C. et al., Nature (London), 1958, 182, 800, (isol)
  9. Gottschalk, G. et al., Nature (London), 1965, 205, 308
  10. Krajewski, D. et al., Phytochemistry, 1997, 45, 1627, (ester glucosides)
  11. Levene, P.A. et al., J. Biol. Chem., 1926, 68, 418, (abs config)
  12. Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MEF500 MKP250
  13. Marchessault, R.H. et al., Makromol. Chem., Macromol. Symp., 1988, 19, 235, (rev, polymers)
  14. Muller, H.-M. et al., Angew. Chem., Int. Ed., 1993, 32, 477, (rev, polymer)
  15. Org. Synth., 1993, 71, 39, (synth, acid, Meester, pmr, ir)
  16. Quang DN, Hashimoto T, Toyota M, Asakawa Y. Occurrence of a high concentration of spider pheromones in the ascomycete fungus Hypoxylon truncatum. J Nat Prod. 2003 Dec;66(12):1613-4.
  17. Schulz S, Toft S. Identification of a sex pheromone from a spider. Science. 1993 Jun 11;260(5114):1635-7.
  18. Seebach, D. et al., Helv. Chim. Acta, 1982, 65, 495-503, (esters, synth)
  19. Seebach, D. et al., Helv. Chim. Acta, 1988, 71, 155, (synth, dimer)
  20. Wipf, B. et al., Helv. Chim. Acta, 1983, 66, 485

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
BDH1
Uniprot ID:
Q02338
Molecular weight:
38156.77
Reactions
(R)-3-Hydroxybutyric acid + NAD → Acetoacetic acid + NADHdetails
(R)-3-Hydroxybutyric acid + NAD → Acetoacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Dehydrogenase that mediates the formation of 2,5-dihydroxybenzoic acid (2,5-DHBA), a siderophore that shares structural similarities with bacterial enterobactin and associates with LCN2, thereby playing a key role in iron homeostasis and transport. Also acts as a 3-hydroxybutyrate dehydrogenase (By similarity).
Gene Name:
BDH2
Uniprot ID:
Q9BUT1
Molecular weight:
26723.57
Reactions
(R)-3-Hydroxybutyric acid + NAD → Acetoacetic acid + NADHdetails
(R)-3-Hydroxybutyric acid + NAD → Acetoacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
DKFZp434G1411
Uniprot ID:
Q9NT06
Molecular weight:
16899.1
References
  1. Gibson KM, Lee CF, Kamali V, Johnston K, Beaudet AL, Craigen WJ, Powell BR, Schwartz R, Tsai MY, Tuchman M: 3-Hydroxy-3-methylglutaryl-CoA lyase deficiency as detected by radiochemical assay in cell extracts by thin-layer chromatography, and identification of three new cases. Clin Chem. 1990 Feb;36(2):297-303. Pubmed: 2302772