General Information of MET (ID: META00257)
Name L-alpha-Aminobutyric acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(+)-2-Aminobutanoate; (+)-2-Aminobutanoic acid; (+)-2-Aminobutyric acid; (+)-alpha-Aminobutyric acid; (-)-2-Aminobutyrate; (-)-2-Aminobutyric acid; (2S)-2-Aminobutanoate; (2S)-2-Aminobutanoic acid; (2S)-2-Aminobutyrate; (2S)-2-Aminobutyric acid; (S)-(+)-alpha-Aminobutyric acid; (S)-2-Amino-butanoate; (S)-2-Amino-butanoic acid; (S)-2-Aminobutanoate; (S)-2-Aminobutanoic acid; (S)-2-Aminobutyrate; (S)-2-Aminobutyric acid; 2-Aminobutanoate; 2-Aminobutanoic acid; 2-Aminobutyrate; 2-Aminobutyric acid; 2S-Amino-butanoate; 2S-Amino-butanoic acid; Butyrine; Butyrine, (+-)-isomer; Butyrine, (R)-isomer; Butyrine, (S)-isomer; Homoalanine; L-(+)-2-Aminobutyrate; L-(+)-2-Aminobutyric acid; L-2-Amino-N-butyric acid; L-2-Aminobutanoate; L-2-Aminobuttersaeure; L-2-Aminobutyrate; L-2-Aminobutyric acid; L-Butyrine; L-Ethylglycine; L-Homoalanine; L-a-Amino-N-butyrate; L-a-Amino-N-butyric acid; L-a-Aminobutyrate; L-a-Aminobutyric acid; L-alpha-Amino-N-butyric acid; S-Butyrine; alpha-Aminobutyric acid; alpha-Aminobutyric acid, (+-)-isomer; alpha-Aminobutyric acid, (R)-isomer; alpha-Aminobutyric acid, (S)-isomer
Source Endogenous;Yeast Metabolite;Fatty acyls;Food;Microbial
Structure Type   Amino acids, peptides, and analogues  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
PubChem CID
80283
HMDB ID
HMDB0000452
Formula
C4H9NO2
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C02356
ChEBI ID
35619
FooDB ID
FDB012537
ChemSpider ID
72524
METLIN ID
12
Physicochemical Properties Molecular Weight 103.12 Topological Polar Surface Area 63.3
XlogP -2.5 Complexity 72.1
Heavy Atom Count 7 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
L-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. alpha-Aminobutyric acid is elevated in the plasma of children with Reye's syndrome, tyrosinemia, homocystinuria, nonketotic hyperglycinemia, and ornithine transcarbamylase deficiency. 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.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            GTPase KRas (KRAS) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of KRAS
                      Induced Change L-alpha-Aminobutyric acid concentration: increase (FC = 2.37)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Lung cancer [ICD-11: 2C25]
                      Details It is reported that overexpression of KRAS leads to the increase of L-alpha-Aminobutyric acid levels compared with control group.
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change L-alpha-Aminobutyric acid concentration: decrease (FC = 0.54 / 0.54)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of L-alpha-Aminobutyric acid levels compared with control group.
References
1 Capturing the metabolomic diversity of KRAS mutants in non-small-cell lung cancer cells. Oncotarget. 2014 Jul 15;5(13):4722-31.
2 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.

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