CHEBI:1148 - 2-hydroxybutyric acid

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ChEBI Name 2-hydroxybutyric acid
ChEBI ID CHEBI:1148
Definition A hydroxybutyric acid having a single hydroxyl group located at position 2; urinary secretion of 2-hydroxybutyric acid is increased with alcohol ingestion or vigorous physical exercise and is associated with lactic acidosis and ketoacidosis in humans and diabetes in animals.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:675746
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Formula C4H8O3
Net Charge 0
Average Mass 104.10450
Monoisotopic Mass 104.047
InChI InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
InChIKey AFENDNXGAFYKQO-UHFFFAOYSA-N
SMILES CCC(O)C(O)=O
Metabolite of Species Details
Chlamydomonas reinhardtii (NCBI:3055) See: PubMed
Homo sapiens (NCBI:9606) See: DOI
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).
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
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ChEBI Ontology
Outgoing 2-hydroxybutyric acid (CHEBI:1148) has functional parent butyric acid (CHEBI:30772)
2-hydroxybutyric acid (CHEBI:1148) has role algal metabolite (CHEBI:84735)
2-hydroxybutyric acid (CHEBI:1148) has role human metabolite (CHEBI:77746)
2-hydroxybutyric acid (CHEBI:1148) is a 2-hydroxy monocarboxylic acid (CHEBI:49302)
2-hydroxybutyric acid (CHEBI:1148) is a hydroxybutyric acid (CHEBI:24684)
2-hydroxybutyric acid (CHEBI:1148) is conjugate acid of 2-hydroxybutyrate (CHEBI:64552)
Incoming (R)-2-hydroxybutyric acid (CHEBI:50612) is a 2-hydroxybutyric acid (CHEBI:1148)
(S)-2-hydroxybutyric acid (CHEBI:50613) is a 2-hydroxybutyric acid (CHEBI:1148)
2-hydroxybutyrate (CHEBI:64552) is conjugate base of 2-hydroxybutyric acid (CHEBI:1148)
IUPAC Name
2-hydroxybutanoic acid
Synonyms Sources
2-Hydroxybutanoic acid KEGG COMPOUND
2-Hydroxybutyric acid ChEMBL
2-Hydroxybutyric acid KEGG COMPOUND
α-hydroxybutanoic acid ChEBI
α-hydroxybutyric acid ChEBI
Database Links Databases
2-Hydroxybutyric_acid Wikipedia
C05984 KEGG COMPOUND
HMDB0000008 HMDB
LMFA01050004 LIPID MAPS
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Registry Numbers Types Sources
600-15-7 CAS Registry Number ChemIDplus
878248 Beilstein Registry Number Beilstein
878248 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15749359 PubMed citation Europe PMC
164303 PubMed citation Europe PMC
168632 PubMed citation Europe PMC
Last Modified
23 October 2015