2-hydroxybutyric acid (CHEBI:1148)

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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

Supplier Information	ChemicalBook:CB8742186, ChemicalBook:CB64796923, eMolecules:514488, ZINC000003645145

Download	Molfile XML SDF

Wikipedia	License
Leucine (symbol Leu or L) is an essential amino acid that is used in the biosynthesis of proteins. Leucine is an α-amino acid, meaning it contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain isobutyl group, making it a non-polar aliphatic amino acid. It is essential in humans, meaning the body cannot synthesize it; it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, and beans and other legumes. It is encoded by the codons UUA, UUG, CUU, CUC, CUA, and CUG. Leucine is named after the Greek word for "white": λευκός (leukós, "white"), after its common appearance as a white powder, a property it shares with many other amino acids. Like valine and isoleucine, leucine is a branched-chain amino acid. The primary metabolic end products of leucine metabolism are acetyl-CoA and acetoacetate; consequently, it is one of the two exclusively ketogenic amino acids, with lysine being the other. It is the most important ketogenic amino acid in humans. Leucine and β-hydroxy β-methylbutyric acid, a minor leucine metabolite, exhibit pharmacological activity in humans and have been demonstrated to promote protein biosynthesis via the phosphorylation of the mechanistic target of rapamycin (mTOR).
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Formula

C4H8O3

Net Charge

Average Mass

104.10450

Monoisotopic Mass

104.04734

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:txid3055)	See: PubMed
Homo sapiens (NCBI:txid9606)	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.

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	2-hydroxybutanoyl-CoA (CHEBI:139303) has functional parent 2-hydroxybutyric acid (CHEBI:1148) (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

Last Modified

14 December 2017