You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.
Record Information
Version1.0
Creation Date2016-09-30 22:07:18 UTC
Update Date2020-05-11 22:52:21 UTC
BMDB IDBMDB0000008
Secondary Accession Numbers
  • BMDB00008
Metabolite Identification
Common Name2-Hydroxybutyric acid
Description2-Hydroxybutyric acid, also known as alpha-hydroxybutyrate or 2-hydroxybutanoate, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. 2-Hydroxybutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 2-Hydroxybutyric acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(S)-2-Hydroxybutanoic acidChEBI
2-HydroxybutyrateChEBI
2-Hydroxybutyric acidChEBI
L-2-Hydroxybutanoic acidChEBI
L-2-Hydroxybutyric acidChEBI
L-alpha-Hydroxybutanoic acidChEBI
L-alpha-Hydroxybutyric acidChEBI
(S)-2-HydroxybutanoateGenerator
L-2-HydroxybutanoateGenerator
L-2-HydroxybutyrateGenerator
L-a-HydroxybutanoateGenerator
L-a-Hydroxybutanoic acidGenerator
L-alpha-HydroxybutanoateGenerator
L-Α-hydroxybutanoateGenerator
L-Α-hydroxybutanoic acidGenerator
L-a-HydroxybutyrateGenerator
L-a-Hydroxybutyric acidGenerator
L-alpha-HydroxybutyrateGenerator
L-Α-hydroxybutyrateGenerator
L-Α-hydroxybutyric acidGenerator
(S)-2-HydroxybutyrateGenerator
2-HydroxybutanoateGenerator
(+)-2-Hydroxy-n-butyric acidHMDB
(+)-2-Hydroxybutanoic acidHMDB
(+)-2-Hydroxybutyric acidHMDB
(+)-alpha-Hydroxybutyric acidHMDB
(+)-α-Hydroxybutyric acidHMDB
(2S)-2-Hydroxybutanoic acidHMDB
(S)-(+)-2-Hydroxybutanoic acidHMDB
(S)-2-Hydroxybutyric acidHMDB
2-Hydroxybutanoic acidHMDB
alpha-Hydroxy-n-butyric acidHMDB
alpha-Hydroxybutanoic acidHMDB
alpha-Hydroxybutyric acidHMDB
α-Hydroxy-n-butyric acidHMDB
α-Hydroxybutanoic acidHMDB
α-Hydroxybutyric acidHMDB
Chemical FormulaC4H8O3
Average Molecular Weight104.105
Monoisotopic Molecular Weight104.047344118
IUPAC Name(2S)-2-hydroxybutanoic acid
Traditional Name(S)-2-hydroxybutyric acid
CAS Registry Number600-15-7
SMILES
CC[C@H](O)C(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyAFENDNXGAFYKQO-VKHMYHEASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha hydroxy acids and derivatives
Alternative Parents
Substituents
  • Fatty acid
  • Alpha-hydroxy 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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point44.2 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.16ALOGPS
logP0.051ChemAxon
logS0.67ALOGPS
pKa (Strongest Acidic)3.99ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.36 m³·mol⁻¹ChemAxon
Polarizability9.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001j-0900000000-44dd1bf8072e5731bac4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00e9-9700000000-93eba027d5343e3d6ce1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-1910000000-3bc9898b26df33cad244View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-4d935da8e593ec61fd96View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001j-0900000000-44dd1bf8072e5731bac4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00e9-9700000000-93eba027d5343e3d6ce1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1910000000-3bc9898b26df33cad244View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-9600000000-f688c3e6fdeb5f0270c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4j-9200000000-e3b371c29b9ebed3199bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfs-9700000000-bccfada2c97e04d34417View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4i-9000000000-4d935da8e593ec61fd96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-2900000000-3c7915ea71886873f024View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0zfr-7900000000-d91c840306a06d4ea513View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-9400000000-7bdf5cb6c5aa8c1d607dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-bf04b472392c16bd165cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-483980f183cd4095b2f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-5900000000-9185cef9251e02ac688cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9200000000-ea836921fe44635e66c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-cf8130e8094c63aa0e25View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Liver
  • Mammary Gland
  • Milk
  • Muscle
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000008
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021867
KNApSAcK IDNot Available
Chemspider ID389701
KEGG Compound IDC05984
BioCyc IDCPD-3564
BiGG IDNot Available
Wikipedia Link2-Hydroxybutyric_acid
METLIN IDNot Available
PubChem Compound440864
PDB IDNot Available
ChEBI ID50613
References
Synthesis ReferenceCarlier, J. P.; Henry, C.; Lorin, V.; Rouffignat, K. Conversion of DL-threonine, D-threonine and 2-oxobutyrate into propionate and 2-hydroxybutyrate by Fusobacterium species. Letters in Applied Microbiology (1997), 25(5), 371-374.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]