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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-23 20:53:47 UTC
Secondary Accession Numbers
  • HMDB0000758
  • HMDB0011597
  • HMDB00442
  • HMDB00758
  • HMDB11597
Metabolite Identification
Common Name(S)-3-Hydroxybutyric acid
Description(S)-3-Hydroxybutyric acid is a normal human metabolite that has been found elevated in geriatric patients remitting from depression (PMID: 17048218 ). 3-Hydroxybutyric acid is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-hydroxybutyric acid are raised in ketosis. In humans, 3-hydroxybutyric acid is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low.
(+)-3-Hydroxybutyric acidChEBI
(3S)-3-Hydroxybutyric acidChEBI
(S)-3-Hydroxybutanoic acidChEBI
(S)-beta-Hydroxybutyric acidChEBI
L-(+)-3-Hydroxybutyric acidChEBI
L-3-Hydroxybutyric acidChEBI
(S)-b-Hydroxybutyric acidGenerator
(S)-Β-hydroxybutyric acidGenerator
(+)-3-Hydroxy-N-butyric acidHMDB
(3S)-3-Hydroxy-butanoic acidHMDB
(S)-3-Hydroxy-2-methyl-propanoic acidHMDB
(S)-3-Hydroxy-butanoic acidHMDB
(S)-b-Hydroxyisobutyric acidHMDB
(S)-beta-Hydroxyisobutyric acidHMDB
L-(+)-2-Methyl-hydracrylic acidHMDB
L-(+)-b-Hydroxyisobutyric acidHMDB
L-(+)-beta-Hydroxyisobutyric acidHMDB
(3S)-3-Hydroxybutanoic acidHMDB
(S)-(+)-beta-Hydroxybutyric acidHMDB
(S)-(+)-β-Hydroxybutyric acidHMDB
(S)-3-Hydroxybutyric acidHMDB
(S)-beta-Hydroxybutanoic acidHMDB
(S)-β-Hydroxybutanoic acidHMDB
3-Hydroxy-n-butyric acidHMDB
3-Hydroxybutanoic acidHMDB
3-Hydroxybutyric acidHMDB
L-beta-Hydroxybutyric acidHMDB
L-β-Hydroxybutyric acidHMDB
beta-Hydroxy-n-butyric acidHMDB
beta-Hydroxybutanoic acidHMDB
beta-Hydroxybutyric acidHMDB
β-Hydroxy-n-butyric acidHMDB
β-Hydroxybutanoic acidHMDB
β-Hydroxybutyric acidHMDB
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name(3S)-3-hydroxybutanoic acid
Traditional Nameβ-hydroxybutyrate,l
CAS Registry Number6168-83-8
InChI Identifier
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
  • 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


Biological location:

Physical Properties
Experimental Properties
Melting Point45 - 48 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility539 g/LALOGPS
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
Polarizability9.94 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9000000000-5f169537ace358b06fd0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ei-9710000000-2652bd46b41e50defdb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a4i-9200000000-4156904e7472b5e97249Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d794440Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9100000000-889e2968ad4fd52cdd92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-9000000000-6c660170b8f4aa6bcd02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c39869c905b7e93b7f97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-9800000000-532ea53160d6ca2efcaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pbi-9200000000-b2c59fd56b1a1d713ea9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-29e8d104108ac71cd640Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Adipose Tissue
  • Brain
  • Neuron
  • Skeletal Muscle
Normal Concentrations
BloodDetected and Quantified20.0 (19.0 - 23.0) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified5.9 umol/mmol creatinineNewborn (0-30 days old)Not SpecifiedNormal details
UrineDetected and Quantified14.0 (1.0-27.0) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
UrineDetected and Quantified1.4 +/- 1.3 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022048
KNApSAcK IDNot Available
Chemspider ID85121
KEGG Compound IDC03197
BioCyc IDCPD-1843
BiGG IDNot Available
Wikipedia LinkBeta-Hydroxybutyric_acid
METLIN IDNot Available
PubChem Compound94318
PDB IDNot Available
ChEBI ID17290
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceZhao, Jun. Synthesis of (S)-b-hydroxybutanoic acid from L-lactic acid. Hecheng Huaxue (1998), 6(4), 442-444.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Byrne HA, Tieszen KL, Hollis S, Dornan TL, New JP: Evaluation of an electrochemical sensor for measuring blood ketones. Diabetes Care. 2000 Apr;23(4):500-3. [PubMed:10857942 ]
  2. Altorjay A, Juhasz A, Kellner V, Sohar G, Fekete M, Sohar I: Metabolic changes in the lower esophageal sphincter influencing the result of anti-reflux surgical interventions in chronic gastroesophageal reflux disease. World J Gastroenterol. 2005 Mar 21;11(11):1623-8. [PubMed:15786538 ]
  3. 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 ]
  4. Eichler A, Forster H, Heller K, Behne M: [Ketoacidosis in a 14 month old child caused by fasting]. Anaesthesist. 1999 Nov;48(11):813-6. [PubMed:10631441 ]
  5. Soroka SD, Chayaraks S, Cheema-Dhadli S, Myers JA, Rubin S, Sonnenberg H, Halperin ML: Minimum urine flow rate during water deprivation: importance of the nonurea versus total osmolality in the inner medulla. J Am Soc Nephrol. 1997 Jun;8(6):880-6. [PubMed:9189853 ]
  6. 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 ]
  7. Baracos VE, Mackenzie ML: Investigations of branched-chain amino acids and their metabolites in animal models of cancer. J Nutr. 2006 Jan;136(1 Suppl):237S-42S. [PubMed:16365090 ]
  8. Nadgir UM, Silver FL, MacGillivray MH: Unrecognized persistence of beta-hydroxybutyrate in diabetic ketoacidosis. Endocr Res. 2001 Feb-May;27(1-2):41-6. [PubMed:11428720 ]
  9. 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 ]
  10. Oosterheert JJ, van de Wiel A: [Ketoacidosis after cessation of chronic alcohol consumption]. Ned Tijdschr Geneeskd. 2002 May 18;146(20):950-4. [PubMed:12051065 ]
  11. Seyfried TN, Mukherjee P: Targeting energy metabolism in brain cancer: review and hypothesis. Nutr Metab (Lond). 2005 Oct 21;2:30. [PubMed:16242042 ]
  12. Fernqvist-Forbes E, Linde B: Insulin absorption, glucose homeostasis, and lipolysis in IDDM during mental stress. Diabetes Care. 1991 Nov;14(11):1006-12. [PubMed:1797480 ]
  13. Noh HS, Hah YS, Nilufar R, Han J, Bong JH, Kang SS, Cho GJ, Choi WS: Acetoacetate protects neuronal cells from oxidative glutamate toxicity. J Neurosci Res. 2006 Mar;83(4):702-9. [PubMed:16435389 ]
  14. Paige LA, Mitchell MW, Krishnan KR, Kaddurah-Daouk R, Steffens DC: A preliminary metabolomic analysis of older adults with and without depression. Int J Geriatr Psychiatry. 2007 May;22(5):418-23. [PubMed:17048218 ]


General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the cofactor-independent reversible oxidation of gamma-hydroxybutyrate (GHB) to succinic semialdehyde (SSA) coupled to reduction of 2-ketoglutarate (2-KG) to D-2-hydroxyglutarate (D-2-HG). D,L-3-hydroxyisobutyrate and L-3-hydroxybutyrate (L-3-OHB) are also substrates for HOT with 10-fold lower activities.
Gene Name:
Uniprot ID:
Molecular weight:
(S)-3-Hydroxybutyric acid + Oxoglutaric acid → Acetoacetic acid + D-2-Hydroxyglutaric aciddetails
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:
Uniprot ID:
Molecular weight: