CHEBI:18261 - N-carbamoyl-β-alanine

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ChEBI Name N-carbamoyl-β-alanine
ChEBI ID CHEBI:18261
ChEBI ASCII Name N-carbamoyl-beta-alanine
Definition A β-alanine derivative that is propionic acid bearing a ureido group at position 3.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:21690, CHEBI:46352, CHEBI:12495, CHEBI:1671
Supplier Information ZINC000008551531
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Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. Lysine contains an α-amino group (which is in the protonated −NH+3 form when the lysine is dissolved in water at physiological pH), an α-carboxylic acid group (which is in the deprotonated −COO− form when the lysine is dissolved in water at physiological pH), and a side chain (CH2)4NH2 (which is partially protonated when the lysine is dissolved in water at physiological pH), and so it is classified as a basic, charged (in water at physiological pH), aliphatic amino acid. It is encoded by the codons AAA and AAG. Like almost all other amino acids, the α-carbon is chiral and lysine may refer to either enantiomer or a racemic mixture of both. For the purpose of this article, lysine will refer to the biologically active enantiomer L-lysine, where the α-carbon is in the S configuration. The human body cannot synthesize lysine. It is essential in humans and must therefore be obtained from the diet. In organisms that synthesise lysine, two main biosynthetic pathways exist, the diaminopimelate and α-aminoadipate pathways, which employ distinct enzymes and substrates and are found in diverse organisms. Lysine catabolism occurs through one of several pathways, the most common of which is the saccharopine pathway. Lysine plays several roles in humans, most importantly proteinogenesis, but also in the crosslinking of collagen polypeptides, uptake of essential mineral nutrients, and in the production of carnitine, which is key in fatty acid metabolism. Lysine is also often involved in histone modifications, and thus, impacts the epigenome. The ε-amino group often participates in hydrogen bonding and as a general base in catalysis. The ε-ammonium group (−NH+3) is attached to the fourth carbon from the α-carbon, which is attached to the carboxyl (−COOH) group. Due to its importance in several biological processes, a lack of lysine can lead to several disease states including defective connective tissues, impaired fatty acid metabolism, anaemia, and systemic protein-energy deficiency. In contrast, an overabundance of lysine, caused by ineffective catabolism, can cause severe neurological disorders. Lysine was first isolated by the German biological chemist Ferdinand Heinrich Edmund Drechsel in 1889 from hydrolysis of the protein casein, and thus named it Lysin, from Greek λύσις (lysis) 'loosening'. In 1902, the German chemists Emil Fischer and Fritz Weigert determined lysine's chemical structure by synthesizing it. The one-letter symbol K was assigned to lysine for being alphabetically nearest, with L being assigned to the structurally simpler leucine, and M to methionine.
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Formula C4H8N2O3
Net Charge 0
Average Mass 132.11800
Monoisotopic Mass 132.05349
InChI InChI=1S/C4H8N2O3/c5-4(9)6-2-1-3(7)8/h1-2H2,(H,7,8)(H3,5,6,9)
InChIKey JSJWCHRYRHKBBW-UHFFFAOYSA-N
SMILES NC(=O)NCCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-carbamoyl-β-alanine (CHEBI:18261) has functional parent propionic acid (CHEBI:30768)
N-carbamoyl-β-alanine (CHEBI:18261) has role metabolite (CHEBI:25212)
N-carbamoyl-β-alanine (CHEBI:18261) has role mouse metabolite (CHEBI:75771)
N-carbamoyl-β-alanine (CHEBI:18261) is a β-alanine derivative (CHEBI:22823)
N-carbamoyl-β-alanine (CHEBI:18261) is conjugate acid of N-carbamoyl-β-alaninate (CHEBI:11892)
Incoming N-carbamoyl-β-alaninate (CHEBI:11892) is conjugate base of N-carbamoyl-β-alanine (CHEBI:18261)
IUPAC Names
3-(carbamoylamino)propanoic acid
N-carbamoyl-β-alanine
Synonyms Sources
3-[(aminocarbonyl)amino]propanoic acid ChEBI
3-Ureidopropanoate KEGG COMPOUND
3-ureidopropanoic acid HMDB
3-Ureidopropionate KEGG COMPOUND
3-Ureidopropionic acid HMDB
beta-Ureidopropionic acid KEGG COMPOUND
N-(AMINOCARBONYL)-BETA-ALANINE PDBeChem
N-(aminocarbonyl)-β-alanine ChemIDplus
N-Carbamoyl-beta-alanine KEGG COMPOUND
N-carbamoyl-beta-alanine PDBeChem
N-carbamoyl-beta-alanine ChEBI
Ureidopropanoic acid ChEBI
Ureidopropionic acid HMDB
Manual Xrefs Databases
3-UREIDO-PROPIONATE MetaCyc
3-Ureidopropionic_acid Wikipedia
C02642 KEGG COMPOUND
HMDB0000026 HMDB
URP PDBeChem
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Registry Numbers Types Sources
1705263 Reaxys Registry Number Reaxys
462-88-4 CAS Registry Number ChemIDplus
675230 Gmelin Registry Number Gmelin
Citations Types Sources
1536562 PubMed citation Europe PMC
17190852 PubMed citation Europe PMC
22770225 PubMed citation Europe PMC
Last Modified
27 January 2016