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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
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 NameNot Available
Traditional NameNot Available
CAS Registry Number625-72-9
SMILESNot Available
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 PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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

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
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