| Alanine (symbol Ala or A), 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 non-polar, 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. The right-handed form, D-alanine, occurs in peptides in some bacterial cell walls: 131 (in peptidoglycan) and in some peptide antibiotics, and occurs in the tissues of many crustaceans and molluscs as an osmolyte. |
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| InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15) |
| QIVBCDIJIAJPQS-UHFFFAOYSA-N |
| NC(Cc1c[nH]c2ccccc12)C(O)=O |
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Daphnia magna
(NCBI:txid35525)
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See:
Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
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View more via ChEBI Ontology
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2-amino-3-(1H-indol-3-yl)propanoic acid
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IUPAC
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alpha-Amino-beta-(3-indolyl)-propionic acid
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KEGG COMPOUND
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α-amino-β-3-indolepropionic acid
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ChEBI
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β-3-indolylalanine
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ChEBI
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Htrp
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IUPAC
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triptófano
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ChEBI
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Trp
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ChEBI
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Tryptophan
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KEGG COMPOUND
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tryptophane
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ChEBI
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W
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ChEBI
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4532
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Gmelin Registry Number
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Gmelin
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54-12-6
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CAS Registry Number
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NIST Chemistry WebBook
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54-12-6
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CAS Registry Number
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ChemIDplus
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86196
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Reaxys Registry Number
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Reaxys
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17439666
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PubMed citation
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Europe PMC
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22264337
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PubMed citation
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Europe PMC
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