Record Information
Version1.0
Creation date2011-09-21 00:04:15 UTC
Update date2018-05-29 01:52:41 UTC
Primary IDFDB021869
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. It 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 . [HMDB]
CAS Number625-72-9
Structure
Thumb
Synonyms
SynonymSource
(R)-(-)-beta-Hydroxybutyric acidChEBI
(R)-3-Hydroxybutanoic acidChEBI
3-D-Hydroxybutyric acidChEBI
D-3-Hydroxybutyric acidChEBI
D-beta-Hydroxybutyric acidKegg
(R)-(-)-b-HydroxybutyrateGenerator
(R)-(-)-b-Hydroxybutyric acidGenerator
(R)-(-)-beta-HydroxybutyrateGenerator
(R)-(-)-Β-hydroxybutyrateGenerator
(R)-(-)-Β-hydroxybutyric acidGenerator
(R)-3-HydroxybutanoateGenerator
3-D-HydroxybutyrateGenerator
D-3-HydroxybutyrateGenerator
D-b-HydroxybutyrateGenerator
D-b-Hydroxybutyric acidGenerator
D-beta-HydroxybutyrateGenerator
D-Β-hydroxybutyrateGenerator
D-Β-hydroxybutyric acidGenerator
(R)-3-HydroxybutyrateGenerator
3-delta-HydroxybutyrateHMDB
3-delta-Hydroxybutyric acidHMDB
BHIBHMDB
D-(-)-3-HydroxybutyrateHMDB
delta-(-)-3-HydroxybutyrateHMDB
delta-3-HydroxybutyrateHMDB
delta-3-Hydroxybutyric acidHMDB
delta-beta-HydroxybutyrateHMDB
3R-Hydroxy-butanoateHMDB
(R)-3-Hydroxybutyric acidKEGG
(R)-(-)-β-hydroxybutyrateGenerator
(R)-(-)-β-hydroxybutyric acidGenerator
3-D-hydroxybutyratehmdb
3-D-hydroxybutyric acidhmdb
3-delta-hydroxybutyratehmdb
3-delta-hydroxybutyric acidhmdb
D-(-)-3-hydroxybutyratehmdb
D-3-hydroxybutyratehmdb
D-3-hydroxybutyric acidhmdb
D-beta-hydroxybutyratehmdb
delta-(-)-3-hydroxybutyratehmdb
delta-3-hydroxybutyratehmdb
delta-3-hydroxybutyric acidhmdb
delta-beta-hydroxybutyratehmdb
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
Polarizability9.96 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H8O3
IUPAC name(3R)-3-hydroxybutanoic acid
InChI IdentifierInChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1
InChI KeyWHBMMWSBFZVSSR-GSVOUGTGSA-N
Isomeric SMILESC[C@@H](O)CC(O)=O
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0900000000-7410b547b9d02c6326c7View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0900000000-7410b547b9d02c6326c7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9000000000-5f169537ace358b06fd0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ei-9710000000-2652bd46b41e50defdb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9200000000-4156904e7472b5e97249View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d794440View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-1900000000-b34932b6f2ee5bca9697View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9100000000-cdbb3586477ed705b4d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-022ab74e163dd752d054View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-18a18150fcc1dfee58cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-e8d8003bcda8aa818d4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1900000000-b34932b6f2ee5bca9697View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9100000000-cdbb3586477ed705b4d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-022ab74e163dd752d054View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-187f6a4024ca6e901188View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-e8d8003bcda8aa818d4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-9100000000-79f60e90c0ce32d976b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9100000000-889e2968ad4fd52cdd92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-9000000000-6c660170b8f4aa6bcd02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c39869c905b7e93b7f97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-9800000000-532ea53160d6ca2efcaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pbi-9200000000-b2c59fd56b1a1d713ea9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-29e8d104108ac71cd640View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID83181
ChEMBL IDCHEMBL1162484
KEGG Compound IDC01089
Pubchem Compound ID92135
Pubchem Substance IDNot Available
ChEBI ID17066
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00011
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36784
KNApSAcK IDNot Available
HET ID3HR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Novel protein similar to 3-hydroxymethyl-3-methylglutaryl-Coenzyme A lyase (Hydroxymethylglutaricaciduria)DKFZp434G1411Q9NT06
Pathways
NameSMPDB LinkKEGG Link
Ketone Body MetabolismSMP00071 map00072
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference