Common Name(2s)-2-aminobutanoate
DescriptionL-alpha-Aminobutyric acid, also known as (S)-2-aminobutanoic acid, homoalanine, 2-AABA, or alpha-Aminobutyric acid, 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. Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. 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 transamination of 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 others are the neurotransmitter gamma-aminobutyric acid (GABA) and beta-aminobutyric acid (BABA) which is known for inducing plant disease resistance.
Structure
Molecular FormulaC4H9NO2
Average Mass103.11980
Monoisotopic Mass103.06333
IUPAC Name(2S)-2-aminobutanoic acid
Traditional Name(-)-2-aminobutyric acid
CAS Registry Number1492-24-6
SMILESCC[C@H]([NH3+])C(=O)[O-]
InChI IdentifierInChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyQWCKQJZIFLGMSD-VKHMYHEASA-N
CHEBI IDCHEBI:74359
HMDB IDHMDB0000452
StateNot Available
Water Solubility3.58e+02 g/l
logP-2.55
logS0.54
pKa (Strongest Acidic)2.62
pKa (Strongest Basic)9.53
Hydrogen Acceptor Count3
Hydrogen Donor Count2
Polar Surface Area63.32 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity25.02 m³·mol⁻¹
Polarizability10.34

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