CHEBI:25017 - leucine

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ChEBI Name leucine ChEBI ID CHEBI:25017 Definition A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the α-carbon is substituted by an isobutyl group. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information ChemicalBook:CB4365169, eMolecules:499483 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License Leucine (symbol Leu or L) is an essential amino acid that is used in the biosynthesis of proteins. Leucine is an α-amino acid, meaning it contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain isobutyl group, making it a non-polar aliphatic amino acid. It is essential in humans, meaning the body cannot synthesize it; it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, and beans and other legumes. It is encoded by the codons UUA, UUG, CUU, CUC, CUA, and CUG. Leucine is named after the Greek word for "white": λευκός (leukós, "white"), after its common appearance as a white powder, a property it shares with many other amino acids. Like valine and isoleucine, leucine is a branched-chain amino acid. The primary metabolic end products of leucine metabolism are acetyl-CoA and acetoacetate; consequently, it is one of the two exclusively ketogenic amino acids, with lysine being the other. It is the most important ketogenic amino acid in humans. Leucine and β-hydroxy β-methylbutyric acid, a minor leucine metabolite, exhibit pharmacological activity in humans and have been demonstrated to promote protein biosynthesis via the phosphorylation of the mechanistic target of rapamycin (mTOR). Read full article at Wikipedia Formula C6H13NO2 Net Charge 0 Average Mass 131.17296 Monoisotopic Mass 131.09463 InChI InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9) InChIKey ROHFNLRQFUQHCH-UHFFFAOYSA-N SMILES CC(C)CC(N)C(O)=O Metabolite of Species Details 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): Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. View more via ChEBI Ontology ChEBI Ontology Outgoing leucine (CHEBI:25017) has part isobutyl group (CHEBI:30356) leucine (CHEBI:25017) has role Daphnia magna metabolite (CHEBI:83056) leucine (CHEBI:25017) is a α-amino acid (CHEBI:33704) leucine (CHEBI:25017) is a branched-chain amino acid (CHEBI:22918) leucine (CHEBI:25017) is conjugate acid of leucinate (CHEBI:32627) leucine (CHEBI:25017) is conjugate base of leucinium (CHEBI:32628) Incoming α-Asp-Leu (CHEBI:68596) has functional parent leucine (CHEBI:25017) β-Asp-Leu (CHEBI:68600) has functional parent leucine (CHEBI:25017) γ-Glu-Leu (CHEBI:68433) has functional parent leucine (CHEBI:25017) 4-hydroxyleucine (CHEBI:144037) has functional parent leucine (CHEBI:25017) 5,5,5-trifluoroleucine (CHEBI:78014) has functional parent leucine (CHEBI:25017) D-leucine (CHEBI:28225) is a leucine (CHEBI:25017) L-leucine (CHEBI:15603) is a leucine (CHEBI:25017) leucinium (CHEBI:32628) is conjugate acid of leucine (CHEBI:25017) leucinate (CHEBI:32627) is conjugate base of leucine (CHEBI:25017) leucine residue (CHEBI:32630) is substituent group from leucine (CHEBI:25017) leucino group (CHEBI:32629) is substituent group from leucine (CHEBI:25017) leucyl group (CHEBI:37904) is substituent group from leucine (CHEBI:25017) IUPAC Name leucine Synonyms Sources (+-)-Leucine ChemIDplus (RS)-Leucine ChemIDplus 2-amino-4-methylpentanoic acid IUPAC DL-Leucine ChemIDplus Hleu IUPAC L ChEBI Leu ChEBI Leucin ChEBI Leuzin ChEBI Manual Xrefs Databases C16439 KEGG COMPOUND Leucine Wikipedia LMFA01100048 LIPID MAPS View more database links Registry Numbers Types Sources 328-39-2 CAS Registry Number ChemIDplus 328-39-2 CAS Registry Number NIST Chemistry WebBook 50203 Gmelin Registry Number Gmelin 636005 Reaxys Registry Number Reaxys Citation Type Source 17439666 PubMed citation Europe PMC Last Modified 02 July 2019