Common NameD-alanine
DescriptionAlanine is a nonessential amino acid made in the body from the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (Branched Chain Amino Acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as regulator in glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine and glycine, is an inhibitory neurotransmitter in the brain. Alanine can be found in some Gram-positive bacteria (PMID:24752840 ).
Structure
Molecular FormulaC3H7NO2
Average Mass89.09320
Monoisotopic Mass89.04768
IUPAC Name(2R)-2-aminopropanoic acid
Traditional NameD-alanine
CAS Registry Number338-69-2
SMILESC[C@@H]([NH3+])C(=O)[O-]
InChI IdentifierInChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1
InChI KeyQNAYBMKLOCPYGJ-UWTATZPHSA-N
CHEBI IDCHEBI:57416
HMDB IDHMDB0001310
StateSolid
Water Solubility4.47e+02 g/l
logP-3.05
logS0.70
pKa (Strongest Acidic)2.47
pKa (Strongest Basic)9.48
Hydrogen Acceptor Count3
Hydrogen Donor Count2
Polar Surface Area63.32 Ų
Rotatable Bond Count1
Physiological Charge0
Formal Charge0
Refractivity20.50 m³·mol⁻¹
Polarizability8.54

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