4-hydroxybutyric acid (CHEBI:30830)

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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

Supplier Information	No supplier information found for this compound.

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Wikipedia	License
γ-Butyrolactone (GBL) or gamma-butyrolactone is an organic compound with the formula O=CO(CH2)3. It is a hygroscopic, colorless, water-miscible liquid with a weak characteristic odor. It is the simplest 4-carbon lactone. It is mainly used as an intermediate in the production of other chemicals, such as N-methyl-2-pyrrolidone. In humans, GBL acts as a prodrug for gamma-hydroxybutyric acid (GHB) and is often used as a recreational drug. GHB acts as a central nervous system (CNS) depressant with effects similar to those of barbiturates.
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Formula

C4H8O3

Net Charge

Average Mass

104.10452

Monoisotopic Mass

104.04734

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.

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 acid 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 base of 4-hydroxybutyric acid (CHEBI:30830)

IUPAC Name

4-hydroxybutanoic acid

Last Modified

20 August 2024

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.