Showing metabocard for (R)-3-Hydroxybutyric acid (BMDB0000011)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:16:28 UTC
Update Date2020-05-20 23:09:49 UTC
BMDB IDBMDB0000011
Secondary Accession Numbers
  • BMDB00011
Metabolite Identification
Common Name(R)-3-Hydroxybutyric acid
Description(R)-3-Hydroxybutyric acid, also known as (R)-3-hydroxybutanoate or 3-D-hydroxybutyrate, 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 (R)-3-Hydroxybutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule (R)-3-Hydroxybutyric acid exists in all living organisms, ranging from bacteria to humans (R)-3-Hydroxybutyric acid can be converted into acetoacetic acid; which is catalyzed by the enzyme (r)-3-hydroxybutyric acid dehydrogenase, mitochondrial. In cattle, (R)-3-hydroxybutyric acid is involved in the metabolic pathway called the ketone body metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
(-)-3-Hydroxy-n-butyric acidHMDB
(-)-3-Hydroxybutyric acidHMDB
(3R)-3-Hydroxybutanoic acidHMDB
(3R)-3-Hydroxybutyric acidHMDB
(3R)-HydroxybutyrateHMDB
(R)-(-)-3-Hydroxybutyric acidHMDB
(R)-beta-Hydroxybutanoic acidHMDB
(R)-beta-Hydroxybutyric acidHMDB
(R)-β-Hydroxybutanoic acidHMDB
(R)-β-Hydroxybutyric acidHMDB
3-Hydroxy-n-butyric acidHMDB
3-Hydroxybutanoic acidHMDB
3-Hydroxybutyric acidHMDB
3R-Hydroxybutanoic acidHMDB
D-(-)-3-Hydroxybutanoic acidHMDB
D-(-)-3-Hydroxybutyric acidHMDB
D-(-)-beta-Hydroxybutyric acidHMDB
D-(-)-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(3R)-3-hydroxybutanoic acid
Traditional Name(-)-3-hydroxybutyric acid
CAS Registry Number625-72-9
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-/m1/s1
InChI KeyWHBMMWSBFZVSSR-GSVOUGTGSA-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
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point49 - 50 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9200000000-b3917779cc00018df7d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-002e-9000000000-d601a5284802b5564ac8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-128801e4b0f2e4d5344bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9100000000-81d99c8d5304bd26a0cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9200000000-fc7c6bb126f183e27ff0View 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
MSMass Spectrum (Electron Ionization)splash10-0007-9000000000-7fc414806153ebd8822cView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000011
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021869
KNApSAcK IDNot Available
Chemspider ID83181
KEGG Compound IDC01089
BioCyc IDCPD-335
BiGG ID36784
Wikipedia LinkBeta-Hydroxybutyric_acid
METLIN IDNot Available
PubChem Compound92135
PDB IDNot Available
ChEBI ID17066
References
Synthesis ReferenceLe Sann, Christine; Munoz, Dulce M.; Saunders, Natalie; Simpson, Thomas J.; Smith, David I.; Soulas, Florilene; Watts, Paul; Willis, Christine L. Assembly intermediates in polyketide biosynthesis: enantioselective syntheses of b-hydroxycarbonyl compounds. Org Biomol Chem. 2005 May 7;3(9):1719-28. Epub 2005 Mar 31. Pubmed: 15858656
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 3-hydroxybutyrate dehydrogenase type 2
General function:
Lipid transport and metabolism
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 assimilation and homeostasis. Plays a role in susceptibility to bacterial infection by providing an assimilable source of iron that is exploited by pathogenic bacteria (By similarity). Also acts as a 3-hydroxybutyrate dehydrogenase (By similarity).
Gene Name:
BDH2
Uniprot ID:
Q3T046
Molecular weight:
26662.0
Enzyme Details
2. D-beta-hydroxybutyrate dehydrogenase, mitochondrial
General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
BDH1
Uniprot ID:
Q02337
Molecular weight:
38391.0
Reactions
(R)-3-Hydroxybutyric acid + NAD → Acetoacetic acid + NADHdetails