Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:35:59 UTC
Update Date2024-04-30 19:31:04 UTC
Metabolite IDMMDBc0000103
Metabolite Identification
Common NameL-alpha-Aminobutyric acid
DescriptionL-alpha-Aminobutyric acid, also known as (S)-2-aminobutanoic acid, homoalanine, 2-AABA, ethylglycine, or L-butyrine, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-Amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-alpha-aminobutyric acid is soluble (in water) and is a moderately acidic compound (based on its pKa). L-alpha-Aminobutyric acid is a non-proteogenic amino acid that can be found in the human kidney, in liver tissues, and in most biofluids or excreta (e.g. feces, breast milk, urine, and blood). Within the cell, L-alpha-aminobutyric acid is primarily located in the cytoplasm. alpha-Aminobutyric acid is biosynthesized by transaminating oxobutyrate, a metabolite in isoleucine biosynthesis. As a non-proteogenic amino acid, alpha-aminobutyric acid can be used by nonribosomal peptide synthases. One example of a nonribosomal peptide containing alpha-aminobutyric acid is ophthalmic acid, which was first isolated from calf lens. alpha-Aminobutyric acid is a non-essential amino acid that is primarily derived from the catabolism of methionine, threonine, and serine. High protein diets can result in significantly higher alpha-aminobutyrate levels in plasma (PMID: 26227325 ). alpha-Aminobutyric acid is elevated in the plasma of children with Reye's syndrome, tyrosinemia, homocystinuria, nonketotic hyperglycinemia, and ornithine transcarbamylase deficiency (PMID: 420125 ). alpha-Aminobutyric acid is one of the three isomers of aminobutyric acid. The two other are the neurotransmitter gamma-aminobutyric acid (GABA) and beta-aminobutyric acid (BABA) which is known for inducing plant disease resistance.
Structure
Synonyms
ValueSource
(-)-2-Aminobutyric acidChEBI
(2S)-2-Aminobutyric acidChEBI
(S)-2-AminobutanoateChEBI
(S)-2-Aminobutanoic acidChEBI
(S)-2-Aminobutyric acidChEBI
L-(+)-2-Aminobutyric acidChEBI
L-2-AminobuttersaeureChEBI
L-2-Aminobutyric acidChEBI
L-alpha-Amino-N-butyric acidChEBI
L-ButyrineChEBI
S-ButyrineChEBI
(-)-2-AminobutyrateGenerator
(2S)-2-AminobutyrateGenerator
(S)-2-AminobutyrateGenerator
L-(+)-2-AminobutyrateGenerator
L-2-AminobutyrateGenerator
L-a-Amino-N-butyrateGenerator
L-a-Amino-N-butyric acidGenerator
L-alpha-Amino-N-butyrateGenerator
L-Α-amino-N-butyrateGenerator
L-Α-amino-N-butyric acidGenerator
L-a-AminobutyrateGenerator
L-a-Aminobutyric acidGenerator
L-alpha-AminobutyrateGenerator
L-Α-aminobutyrateGenerator
L-Α-aminobutyric acidGenerator
(+)-2-AminobutanoateHMDB
(+)-2-Aminobutanoic acidHMDB
(+)-2-Aminobutyric acidHMDB
(+)-alpha-Aminobutyric acidHMDB
(2S)-2-AminobutanoateHMDB
(2S)-2-Aminobutanoic acidHMDB, MeSH
(S)-(+)-alpha-Aminobutyric acidHMDB
(S)-2-amino-ButanoateHMDB
(S)-2-amino-Butanoic acidHMDB
2-AminobutanoateHMDB
2-Aminobutanoic acidHMDB, MeSH
2-AminobutyrateHMDB
2S-amino-ButanoateHMDB, Generator
2S-amino-Butanoic acidHMDB
alpha-Aminobutyric acidHMDB, MeSH
L-2-amino-N-Butyric acidHMDB
L-EthylglycineHMDB
Butyrine, (R)-isomerMeSH, HMDB
2-Aminobutyric acidMeSH, HMDB, Generator
alpha-Aminobutyric acid, (+-)-isomerMeSH, HMDB
ButyrineMeSH, HMDB
Butyrine, (S)-isomerMeSH, HMDB
L-HomoalanineMeSH, HMDB
alpha-Aminobutyric acid, (S)-isomerMeSH, HMDB
HomoalanineMeSH, HMDB
alpha-Aminobutyric acid, (R)-isomerMeSH, HMDB
Butyrine, (+-)-isomerMeSH, HMDB
L-2-AminobutanoateGenerator, HMDB
Molecular FormulaC4H9NO2
Average Mass103.1198
Monoisotopic Mass103.063328537
IUPAC Name(2S)-2-aminobutanoic acid
Traditional Name(-)-2-aminobutyric acid
CAS Registry Number1492-24-6
SMILES
CC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyQWCKQJZIFLGMSD-VKHMYHEASA-N