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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:40 UTC
HMDB IDHMDB00442
Secondary Accession Numbers
  • 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.
Structure
Thumb
Synonyms
ValueSource
(+)-3-Hydroxybutyric acidChEBI
(3S)-3-Hydroxybutyric acidChEBI
(S)-3-Hydroxybutanoic acidChEBI
(S)-3HbChEBI
(S)-beta-Hydroxybutyric acidChEBI
L-(+)-3-Hydroxybutyric acidChEBI
L-3-Hydroxybutyric acidChEBI
(+)-3-Hydroxy-N-butyric acidHMDB
(3S)-3-Hydroxy-butanoateHMDB
(3S)-3-Hydroxy-butanoic acidHMDB
(S)-3-Hydroxy-2-methyl-propanoateHMDB
(S)-3-Hydroxy-2-methyl-propanoic acidHMDB
(S)-3-Hydroxy-butanoateHMDB
(S)-3-Hydroxy-butanoic acidHMDB
(S)-3-HydroxybutanoateHMDB
(S)-3-HydroxybutyrateHMDB
(S)-b-HydroxyisobutyrateHMDB
(S)-b-Hydroxyisobutyric acidHMDB
(S)-beta-HydroxyisobutyrateHMDB
(S)-beta-Hydroxyisobutyric acidHMDB
L-(+)-2-Methyl-hydracrylateHMDB
L-(+)-2-Methyl-hydracrylic acidHMDB
L-(+)-b-HydroxyisobutyrateHMDB
L-(+)-b-Hydroxyisobutyric acidHMDB
L-(+)-beta-HydroxyisobutyrateHMDB
L-(+)-beta-Hydroxyisobutyric acidHMDB
L-beta-HydroxybutyrateHMDB
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
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-/m0/s1
InChI KeyInChIKey=WHBMMWSBFZVSSR-VKHMYHEASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point45 - 48 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility539.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.46 m3·mol-1ChemAxon
Polarizability9.94 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a4i-9200000000-4156904e7472b5e97249View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d794440View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Adipose Tissue
  • Brain
  • Muscle
  • Neuron
  • Skeletal Muscle
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 ...
details
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022048
KNApSAcK IDNot Available
Chemspider ID85121
KEGG Compound IDC03197
BioCyc IDCPD-1843
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00442
Metagene LinkHMDB00442
METLIN IDNot Available
PubChem Compound94318
PDB ID3HL
ChEBI ID17290
References
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. 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. [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. [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. [12149510 ]
  4. 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. [10857942 ]
  5. 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. [15786538 ]
  6. 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. [10631441 ]
  7. 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. [9189853 ]
  8. 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. [16365090 ]
  9. Nadgir UM, Silver FL, MacGillivray MH: Unrecognized persistence of beta-hydroxybutyrate in diabetic ketoacidosis. Endocr Res. 2001 Feb-May;27(1-2):41-6. [11428720 ]
  10. Oosterheert JJ, van de Wiel A: [Ketoacidosis after cessation of chronic alcohol consumption] Ned Tijdschr Geneeskd. 2002 May 18;146(20):950-4. [12051065 ]
  11. Seyfried TN, Mukherjee P: Targeting energy metabolism in brain cancer: review and hypothesis. Nutr Metab (Lond). 2005 Oct 21;2:30. [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. [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. [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. [17048218 ]

Enzymes

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:
ADHFE1
Uniprot ID:
Q8IWW8
Molecular weight:
50307.42
Reactions
(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:
BDH2
Uniprot ID:
Q9BUT1
Molecular weight:
26723.57