CHEBI:16927 - L-saccharopine

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ChEBI Name L-saccharopine
ChEBI ID CHEBI:16927
ChEBI ASCII Name L-saccharopine
Definition The N6-(1,3-dicarboxypropan-1-yl) derivative of L-lysine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45721, CHEBI:7406, CHEBI:12660, CHEBI:21861
Supplier Information No supplier information found for this compound.
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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 C11H20N2O6
Net Charge 0
Average Mass 276.28630
Monoisotopic Mass 276.13214
InChI InChI=1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1
InChIKey ZDGJAHTZVHVLOT-YUMQZZPRSA-N
SMILES N[C@@H](CCCCN[C@@H](CCC(O)=O)C(O)=O)C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Roles Classification
Biological Role(s): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
(via opine )
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ChEBI Ontology
Outgoing L-saccharopine (CHEBI:16927) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
L-saccharopine (CHEBI:16927) has role human metabolite (CHEBI:77746)
L-saccharopine (CHEBI:16927) has role mouse metabolite (CHEBI:75771)
L-saccharopine (CHEBI:16927) is a L-lysine derivative (CHEBI:25095)
L-saccharopine (CHEBI:16927) is a amino acid opine (CHEBI:83229)
L-saccharopine (CHEBI:16927) is conjugate acid of L-saccharopinate(1−) (CHEBI:57951)
Incoming L-saccharopinate(1−) (CHEBI:57951) is conjugate base of L-saccharopine (CHEBI:16927)
IUPAC Name
N-[(5S)-5-amino-5-carboxypentyl]-L-glutamic acid
Synonyms Sources
epsilon-N-(L-Glutar-2-yl)-L-lysine ChemIDplus
L-Saccharopine KEGG COMPOUND
N-[(S)-5-Amino-5-carboxypentyl]-L-glutamic acid KEGG COMPOUND
N6-(L-1,3-Dicarboxypropyl)-L-lysine KEGG COMPOUND
Saccharopine KEGG COMPOUND
Manual Xrefs Databases
C00007227 KNApSAcK
C00449 KEGG COMPOUND
HMDB0000279 HMDB
Saccharopine Wikipedia
SACCHAROPINE MetaCyc
SHR PDBeChem
View more database links
Registry Numbers Types Sources
3063139 Reaxys Registry Number Reaxys
997-68-2 CAS Registry Number KEGG COMPOUND
997-68-2 CAS Registry Number ChemIDplus
Citations Types Sources
22449979 PubMed citation Europe PMC
22862918 PubMed citation Europe PMC
Last Modified
26 May 2016