CHEBI:18237 - glutamic acid

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ChEBI Name glutamic acid ChEBI ID CHEBI:18237 Definition An α-amino acid that is glutaric acid bearing a single amino substituent at position 2. Stars This entity has been manually annotated by the ChEBI Team. Secondary ChEBI IDs CHEBI:24314, CHEBI:5431 Supplier Information ChemicalBook:CB5116317, eMolecules:498263 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License Glutamic acid (symbol Glu or E; known as glutamate in its anionic form) is an α-amino acid that is used by almost all living beings in the biosynthesis of proteins. It is a non-essential nutrient for humans, meaning that the human body can synthesize enough for its use. It is also the most abundant excitatory neurotransmitter in the vertebrate nervous system. It serves as the precursor for the synthesis of the inhibitory gamma-aminobutyric acid (GABA) in GABAergic neurons. Its molecular formula is C5H9NO4. Glutamic acid exists in two optically isomeric forms; the dextrorotatory L-form is usually obtained by hydrolysis of gluten or from the waste waters of beet-sugar manufacture or by fermentation. Its molecular structure could be idealized as HOOC−CH(NH2)−(CH2)2−COOH, with two carboxyl groups −COOH and one amino group −NH2. However, in the solid state and mildly acidic water solutions, the molecule assumes an electrically neutral zwitterion structure −OOC−CH(NH+3)−(CH2)2−COOH. It is encoded by the codons GAA or GAG. The acid can lose one proton from its second carboxyl group to form the conjugate base, the singly-negative anion glutamate −OOC−CH(NH+3)−(CH2)2−COO−. This form of the compound is prevalent in neutral solutions. The glutamate neurotransmitter plays the principal role in neural activation. This anion creates the savory umami flavor of foods and is found in glutamate flavorings such as monosodium glutamate (MSG). In Europe, it is classified as food additive E620. In highly alkaline solutions the doubly negative anion −OOC−CH(NH2)−(CH2)2−COO− prevails. The radical corresponding to glutamate is called glutamyl. The one-letter symbol E for glutamate was assigned as the letter following D for aspartate, as glutamate is larger by one methylene –CH2– group. Read full article at Wikipedia Formula C5H9NO4 Net Charge 0 Average Mass 147.12930 Monoisotopic Mass 147.05316 InChI InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10) InChIKey WHUUTDBJXJRKMK-UHFFFAOYSA-N SMILES NC(CCC(O)=O)C(O)=O Metabolite of Species Details Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed Daphnia magna (NCBI:txid35525) 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 Roles Classification Chemical Role(s): 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 ) Biological Role(s): fundamental metabolite Any metabolite produced by all living cells. View more via ChEBI Ontology ChEBI Ontology Outgoing glutamic acid (CHEBI:18237) has part 2-carboxyethyl group (CHEBI:50329) glutamic acid (CHEBI:18237) has role fundamental metabolite (CHEBI:78675) glutamic acid (CHEBI:18237) is a α-amino acid (CHEBI:33704) glutamic acid (CHEBI:18237) is a polar amino acid (CHEBI:26167) glutamic acid (CHEBI:18237) is conjugate acid of glutamate(1−) (CHEBI:14321) Incoming γ-Glu-Leu (CHEBI:68433) has functional parent glutamic acid (CHEBI:18237) γ-glutamyl-Se-methylselenocysteine (CHEBI:28776) has functional parent glutamic acid (CHEBI:18237) γ-glutamylphenylalanine (CHEBI:82966) has functional parent glutamic acid (CHEBI:18237) γ-glutamylthreonine (CHEBI:82968) has functional parent glutamic acid (CHEBI:18237) γGluCys(IAN)Glu (CHEBI:64978) has functional parent glutamic acid (CHEBI:18237) glutamic acid derivative (CHEBI:24315) has functional parent glutamic acid (CHEBI:18237) D-glutamic acid (CHEBI:15966) is a glutamic acid (CHEBI:18237) L-glutamic acid (CHEBI:16015) is a glutamic acid (CHEBI:18237) glutamate(1−) (CHEBI:14321) is conjugate base of glutamic acid (CHEBI:18237) α-glutamyl group (CHEBI:22453) is substituent group from glutamic acid (CHEBI:18237) γ-glutamyl group (CHEBI:24190) is substituent group from glutamic acid (CHEBI:18237) glutamic acid residue (CHEBI:32483) is substituent group from glutamic acid (CHEBI:18237) glutamo group (CHEBI:24321) is substituent group from glutamic acid (CHEBI:18237) glutamoyl group (CHEBI:24322) is substituent group from glutamic acid (CHEBI:18237) IUPAC Names 2-aminopentanedioic acid glutamic acid Synonyms Sources 2-Aminoglutaric acid KEGG COMPOUND DL-Glutamic acid KEGG DRUG DL-Glutaminic acid KEGG COMPOUND E ChEBI Glu ChEBI Glutamate KEGG COMPOUND Glutamic acid KEGG COMPOUND Glutaminic acid KEGG COMPOUND Glutaminsäure ChEBI Manual Xrefs Databases C00001358 KNApSAcK C00019577 KNApSAcK C00302 KEGG COMPOUND D04341 KEGG DRUG Glutamic_acid Wikipedia View more database links Registry Numbers Types Sources 101971 Gmelin Registry Number Gmelin 1723799 Reaxys Registry Number Reaxys 617-65-2 CAS Registry Number ChemIDplus 617-65-2 CAS Registry Number NIST Chemistry WebBook Citations Last Modified 18 April 2024