CHEBI:20067 - 3-hydroxybutyric acid

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ChEBI Name 3-hydroxybutyric acid
ChEBI ID CHEBI:20067
Definition A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C4H8O3
Net Charge 0
Average Mass 104.10452
Monoisotopic Mass 104.04734
InChI InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
InChIKey WHBMMWSBFZVSSR-UHFFFAOYSA-N
SMILES CC(O)CC(O)=O
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).
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ChEBI Ontology
Outgoing 3-hydroxybutyric acid (CHEBI:20067) has functional parent butyric acid (CHEBI:30772)
3-hydroxybutyric acid (CHEBI:20067) has role human metabolite (CHEBI:77746)
3-hydroxybutyric acid (CHEBI:20067) is a (ω−1)-hydroxy fatty acid (CHEBI:78954)
3-hydroxybutyric acid (CHEBI:20067) is a 3-hydroxy monocarboxylic acid (CHEBI:35969)
3-hydroxybutyric acid (CHEBI:20067) is a hydroxybutyric acid (CHEBI:24684)
3-hydroxybutyric acid (CHEBI:20067) is conjugate acid of 3-hydroxybutyrate (CHEBI:37054)
Incoming (R)-3-hydroxybutyrylcarnitine (CHEBI:84842) has functional parent 3-hydroxybutyric acid (CHEBI:20067)
3-hydroxybutanoyl-CoA (CHEBI:37050) has functional parent 3-hydroxybutyric acid (CHEBI:20067)
curtisian C (CHEBI:65698) has functional parent 3-hydroxybutyric acid (CHEBI:20067)
curtisian D (CHEBI:65699) has functional parent 3-hydroxybutyric acid (CHEBI:20067)
ethyl 3-hydroxybutyrate (CHEBI:87685) has functional parent 3-hydroxybutyric acid (CHEBI:20067)
fleephilone (CHEBI:65900) has functional parent 3-hydroxybutyric acid (CHEBI:20067)
(R)-3-hydroxybutyric acid (CHEBI:17066) is a 3-hydroxybutyric acid (CHEBI:20067)
(S)-3-hydroxybutyric acid (CHEBI:17290) is a 3-hydroxybutyric acid (CHEBI:20067)
3-hydroxybutyrate (CHEBI:37054) is conjugate base of 3-hydroxybutyric acid (CHEBI:20067)
IUPAC Name
3-hydroxybutanoic acid
Synonyms Sources
(1)-3-Hydroxybutyric acid ChemIDplus
3 HBA ChemIDplus
3-Hydroxybuttersaeure ChemIDplus
3-OH-butyric acid ChEBI
β-hydroxy-n-butyric acid ChemIDplus
beta-Hydroxy-n-butyric acid HMDB
β-hydroxybutanoic acid ChEBI
beta-Hydroxybuttersaeure ChemIDplus
β-hydroxybutyric acid ChemIDplus
BHBA ChEBI
DL-beta-Hydroxybutyric acid ChemIDplus
Manual Xrefs Databases
3-hydroxybutyrate Wikipedia
HMDB0000357 HMDB
LMFA01050005 LIPID MAPS
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Registry Numbers Types Sources
300-85-6 CAS Registry Number ChemIDplus
773861 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10855969 PubMed citation Europe PMC
17190852 PubMed citation Europe PMC
17579249 PubMed citation Europe PMC
6061736 PubMed citation Europe PMC
Last Modified
23 October 2015