(S)-3-Hydroxybutyric acid (CHEM021625)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:08:34 UTC
Update Date2016-11-09 01:17:19 UTC
Accession NumberCHEM021625
Identification
Common Name(S)-3-Hydroxybutyric acid
ClassSmall Molecule
DescriptionThe S-enantiomer of 3-hydroxybutyric acid; a normal human metabolite, that has been found elevated in geriatric patients remitting from depression.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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-HydroxybutyrateGenerator
(3S)-3-HydroxybutyrateGenerator
(S)-3-HydroxybutanoateGenerator
(S)-b-HydroxybutyrateGenerator
(S)-b-Hydroxybutyric acidGenerator
(S)-beta-HydroxybutyrateGenerator
(S)-Β-hydroxybutyrateGenerator
(S)-Β-hydroxybutyric acidGenerator
L-(+)-3-HydroxybutyrateGenerator
L-3-HydroxybutyrateGenerator
(S)-3-HydroxybutyrateGenerator
(+)-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)-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
(3S)-3-Hydroxybutanoic acidHMDB
(S)-(+)-beta-Hydroxybutyric acidHMDB
(S)-(+)-Β-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
(S)-3-Hydroxybutyric acidHMDB
Chemical FormulaC4H8O3
Average Molecular Mass104.105 g/mol
Monoisotopic Mass104.047 g/mol
CAS Registry Number6168-83-8
IUPAC Name(3S)-3-hydroxybutanoic acid
Traditional Nameβ-hydroxybutyrate,l
SMILESC[C@H](O)CC(O)=O
InChI IdentifierInChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyWHBMMWSBFZVSSR-VKHMYHEASA-N
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
Substituents
  • 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 Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.46 m³·mol⁻¹ChemAxon
Polarizability9.94 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-de698d113a869245219aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-d964762034ff3766529fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-1c4d36fa24f00e6e9f6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9200000000-61512767fe2a2778ee8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-0006bf28af00ac9af39cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-58f5546067f0f7cf64bbSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000442
FooDB IDFDB022048
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-1843
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBeta-Hydroxybutyric_acid
Chemspider ID85121
ChEBI ID17290
PubChem Compound ID94318
Kegg Compound IDC03197
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17048218
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18461320
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19304817
4. Zhao, Jun. Synthesis of (S)-b-hydroxybutanoic acid from L-lactic acid. Hecheng Huaxue (1998), 6(4), 442-444.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. Nadgir UM, Silver FL, MacGillivray MH: Unrecognized persistence of beta-hydroxybutyrate in diabetic ketoacidosis. Endocr Res. 2001 Feb-May;27(1-2):41-6.
13. 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.
14. Oosterheert JJ, van de Wiel A: [Ketoacidosis after cessation of chronic alcohol consumption]. Ned Tijdschr Geneeskd. 2002 May 18;146(20):950-4.
15. Seyfried TN, Mukherjee P: Targeting energy metabolism in brain cancer: review and hypothesis. Nutr Metab (Lond). 2005 Oct 21;2:30.
16. Fernqvist-Forbes E, Linde B: Insulin absorption, glucose homeostasis, and lipolysis in IDDM during mental stress. Diabetes Care. 1991 Nov;14(11):1006-12.
17. 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.
18. 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.