CHEBI:30830 - 4-hydroxybutyric acid

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ChEBI Name 4-hydroxybutyric acid
ChEBI ID CHEBI:30830
Definition A 4-hydroxy monocarboxylic acid that is butyric acid in which one of the hydrogens at position 4 is replaced by a hydroxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:386065, CHEBI:1860, CHEBI:20402
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Formula C4H8O3
Net Charge 0
Average Mass 104.10452
Monoisotopic Mass 104.047
InChI InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)
InChIKey SJZRECIVHVDYJC-UHFFFAOYSA-N
SMILES OCCCC(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): GHB receptor agonist
A drug that binds to and activates gamma-hydroxybutyric acid receptors.
neurotoxin
A poison that interferes with the functions of the nervous system.
Application(s): general anaesthetic
Substance that produces loss of consciousness.
GHB receptor agonist
A drug that binds to and activates gamma-hydroxybutyric acid receptors.
sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 4-hydroxybutyric acid (CHEBI:30830) has functional parent butyric acid (CHEBI:30772)
4-hydroxybutyric acid (CHEBI:30830) has role general anaesthetic (CHEBI:38869)
4-hydroxybutyric acid (CHEBI:30830) has role GHB receptor agonist (CHEBI:53353)
4-hydroxybutyric acid (CHEBI:30830) has role neurotoxin (CHEBI:50910)
4-hydroxybutyric acid (CHEBI:30830) has role sedative (CHEBI:35717)
4-hydroxybutyric acid (CHEBI:30830) is a 4-hydroxy monocarboxylic acid (CHEBI:35970)
4-hydroxybutyric acid (CHEBI:30830) is a hydroxybutyric acid (CHEBI:24684)
4-hydroxybutyric acid (CHEBI:30830) is conjugate base of 4-hydroxybutyrate (CHEBI:16724)
Incoming 4-hydroxybutyryl-CoA (CHEBI:28522) has functional parent 4-hydroxybutyric acid (CHEBI:30830)
mono(3-carboxypropyl) phthalate (CHEBI:132872) has functional parent 4-hydroxybutyric acid (CHEBI:30830)
4-hydroxybutyrate (CHEBI:16724) is conjugate acid of 4-hydroxybutyric acid (CHEBI:30830)
IUPAC Name
4-hydroxybutanoic acid
Synonyms Sources
3-carboxypropoxy acid ChEBI
4-hydroxy-butyric acid LIPID MAPS
4-Hydroxyalkanoic acid KEGG COMPOUND
4-Hydroxybutanoate KEGG COMPOUND
4-Hydroxybutanoic acid KEGG COMPOUND
4-Hydroxybutyric acid KEGG COMPOUND
4-Hydroxycarboxylic acid KEGG COMPOUND
Gamma Hydroxybutyric Acid DrugBank
gamma-Hydroxybutyric acid DrugBank
γ-hydroxybutyric acid ChEBI
GHB DrugBank
oxy-n-butyric acid ChEBI
Xyrem DrugBank
Database Links Databases
C00989 KEGG COMPOUND
C01991 KEGG COMPOUND
DB01440 DrugBank
LMFA01050006 LIPID MAPS
Oxybate Wikipedia
View more database links
Registry Numbers Types Sources
1720582 Beilstein Registry Number Beilstein
1720582 Reaxys Registry Number Reaxys
591-81-1 CAS Registry Number KEGG COMPOUND
591-81-1 CAS Registry Number ChemIDplus
591-81-1 CAS Registry Number DrugBank
591-81-1 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
15927467 PubMed citation ChEMBL
3361576 PubMed citation ChEMBL
Last Modified
29 July 2016
General Comment
2010-12-30 4-hydroxybutyric acid finds application as a central nervous system depressant that reduces excessive daytime sleepiness and cataplexy in patients with narcolepsy.