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CHEBI:17066 - (R)-3-hydroxybutyric acid

ChEBI IDCHEBI:17066
ChEBI Name(R)-3-hydroxybutyric acid
Stars
ASCII Name(R)-3-hydroxybutyric acid
DefinitionThe R-enantiomer of 3-hydroxybutyric acid. Involved in the synthesis and degradation of ketone bodies, it can be used as an energy source by the brain during hypoglycaemia, and for the synthesis of biodegradable plastics. It is a sex pheremone in the European spider Linyphia triangularis.
Secondary ChEBI IDsCHEBI:322, CHEBI:18666
Last Modified8 March 2018
DownloadsMolfile
FormulaC4H8O3
Net Charge0
Average Mass104.105
Monoisotopic Mass104.04734
SMILESC[C@@H](O)CC(=O)O
InChIInChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1
InChIKeyWHBMMWSBFZVSSR-GSVOUGTGSA-N
Species of MetaboliteComponentSourceComments
Annulohypoxylon truncatum (ncbitaxon:327061) - PubMed (14695807)
Linyphia triangularis (ncbitaxon:94031) - PubMed (17810206)
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
pheromone  A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
(R)-3-hydroxybutyric acid (CHEBI:17066) has role fungal metabolite (CHEBI:76946)
(R)-3-hydroxybutyric acid (CHEBI:17066) has role human metabolite (CHEBI:77746)
(R)-3-hydroxybutyric acid (CHEBI:17066) has role pheromone (CHEBI:26013)
(R)-3-hydroxybutyric acid (CHEBI:17066) is a 3-hydroxybutyric acid (CHEBI:20067)
(R)-3-hydroxybutyric acid (CHEBI:17066) is a ketone body (CHEBI:73693)
(R)-3-hydroxybutyric acid (CHEBI:17066) is conjugate acid of (R)-3-hydroxybutyrate (CHEBI:10983)
(R)-3-hydroxybutyric acid (CHEBI:17066) is enantiomer of (S)-3-hydroxybutyric acid (CHEBI:17290)
Incoming Relation(s)
(R)-3-hydroxybutanoyl-CoA (CHEBI:15452) has functional parent (R)-3-hydroxybutyric acid (CHEBI:17066)
(3R)-3-hydroxybutanoic acid oligomer (CHEBI:140392) has functional parent (R)-3-hydroxybutyric acid (CHEBI:17066)
ascr#11 (CHEBI:78743) has functional parent (R)-3-hydroxybutyric acid (CHEBI:17066)
ethyl (R)-3-hydroxybutanoate (CHEBI:28707) has functional parent (R)-3-hydroxybutyric acid (CHEBI:17066)
(R)-3-hydroxybutyrate (CHEBI:10983) is conjugate base of (R)-3-hydroxybutyric acid (CHEBI:17066)
(S)-3-hydroxybutyric acid (CHEBI:17290) is enantiomer of (R)-3-hydroxybutyric acid (CHEBI:17066)
IUPAC Name 
(3R)-3-hydroxybutanoic acid
Synonyms  Source
(R)-3-Hydroxybutanoic acidKEGG COMPOUND
(R)-3-Hydroxybutyric acidKEGG COMPOUND
(R)-(-)-β-hydroxybutyric acidChEBI
3-D-hydroxybutyric acidChEBI
D-3-hydroxybutyric acidChEBI
Manual XrefsDatabases
C01089KEGG COMPOUND
LMFA01050243LIPID MAPS
HMDB0000011HMDB
CPD-335MetaCyc
WO9312254Patent
Registry NumbersSources
Reaxys:1720568Reaxys
CAS:625-72-9ChemIDplus
CAS:625-72-9KEGG COMPOUND
Citations