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

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (R)-3-hydroxybutyric acid
ChEBI ID CHEBI:17066
ChEBI ASCII Name (R)-3-hydroxybutyric acid
Definition The 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:322, CHEBI:18666
Supplier Information
Download Molfile XML SDF
Formula C4H8O3
Net Charge 0
Average Mass 104.10450
Monoisotopic Mass 104.047
InChI InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1
InChIKey WHBMMWSBFZVSSR-GSVOUGTGSA-N
SMILES C[C@@H](O)CC(O)=O
Metabolite of Species Details
Annulohypoxylon truncatum (NCBI:txid327061) See: PubMed
Linyphia triangularis (NCBI:txid94031) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via 3-hydroxybutyric acid )
pheromone
A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via ketone body )
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
(via ketone body )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (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 (3R)-3-hydroxybutanoic acid oligomer (CHEBI:140392) has functional parent (R)-3-hydroxybutyric acid (CHEBI:17066)
(R)-3-hydroxybutanoyl-CoA (CHEBI:15452) 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 Sources
(R)-(-)-β-hydroxybutyric acid ChEBI
(R)-3-Hydroxybutanoic acid KEGG COMPOUND
(R)-3-Hydroxybutyric acid KEGG COMPOUND
3-D-hydroxybutyric acid ChEBI
D-3-hydroxybutyric acid ChEBI
Database Links Databases
C01089 KEGG COMPOUND
CPD-335 MetaCyc
HMDB0000011 HMDB
LMFA01050243 LIPID MAPS
WO9312254 Patent
View more database links
Registry Numbers Types Sources
1720568 Reaxys Registry Number Reaxys
625-72-9 CAS Registry Number KEGG COMPOUND
625-72-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17810206 PubMed citation Europe PMC
19304817 PubMed citation Europe PMC
20699574 PubMed citation Europe PMC
3679704 PubMed citation Europe PMC
Last Modified
08 March 2018