![]() Skeletal formula of L-alanine (neutral form)
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Names | |||
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IUPAC name
Alanine[1]
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Systematic IUPAC name
2-Aminopropanoic acid | |||
Other names
Alanic acid
Alaninic acid 2-Aminopropionic acid | |||
Identifiers | |||
3D model (JSmol)
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3DMet |
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1720248 | |||
ChEBI |
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ChEMBL |
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ChemSpider | |||
DrugBank |
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ECHA InfoCard | 100.000.249 | ||
EC Number |
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49628 | |||
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KEGG | |||
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |||
C3H7NO2 | |||
Molar mass | 89.094 g·mol−1 | ||
Appearance | white powder | ||
Density | 1.424 g/cm3 | ||
Melting point | 258 °C (496 °F; 531 K) (sublimes) | ||
167.2 g/L (25 °C) | |||
log P | −0.68[2] | ||
Acidity (pKa) |
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−50.5×10−6 cm3/mol | |||
Supplementary data page | |||
Alanine (data page) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Alanine (symbol Ala or A),[4] or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group side chain. Consequently it is classified as a nonpolar, aliphatic α-amino acid. Under biological conditions, it exists in its zwitterionic form with its amine group protonated (as −NH+3) and its carboxyl group deprotonated (as −CO−2). It is non-essential to humans as it can be synthesized metabolically and does not need to be present in the diet. It is encoded by all codons starting with GC (GCU, GCC, GCA, and GCG).
The L-isomer of alanine (left-handed) is the one that is incorporated into proteins. L-alanine is second only to L-leucine in rate of occurrence, accounting for 7.8% of the primary structure in a sample of 1,150 proteins.[5] The right-handed form, D-alanine, occurs in peptides in some bacterial cell walls[6]: 131 (in peptidoglycan) and in some peptide antibiotics, and occurs in the tissues of many crustaceans and molluscs as an osmolyte.[7]