CHEBI:59963 - methylglyoxal-lysine dimer

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ChEBI Name methylglyoxal-lysine dimer
ChEBI ID CHEBI:59963
Definition An imidazolium ion formed via cyclo-dimerisation of L-lysine and methylglyoxal.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C16H29N4O4
Net Charge +1
Average Mass 341.42590
Monoisotopic Mass 341.21833
InChI InChI=1S/C16H28N4O4/c1-12-10-19(8-4-2-6-13(17)15(21)22)11-20(12)9-5-3-7-14(18)16(23)24/h10-11,13-14H,2-9,17-18H2,1H3,(H-,21,22,23,24)/p+1/t13-,14-/m0/s1
InChIKey NVJLIMSDAPOFHF-KBPBESRZSA-O
SMILES Cc1cn(CCCC[C@H](N)C(O)=O)c[n+]1CCCC[C@H](N)C(O)=O
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): epitope
The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via L-alpha-amino acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing methylglyoxal-lysine dimer (CHEBI:59963) has role epitope (CHEBI:53000)
methylglyoxal-lysine dimer (CHEBI:59963) is a L-lysine derivative (CHEBI:25095)
methylglyoxal-lysine dimer (CHEBI:59963) is a imidazolium ion (CHEBI:59964)
methylglyoxal-lysine dimer (CHEBI:59963) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
IUPAC Names
1,3-bis[(5S)-5-amino-5-carboxypentyl]-4-methyl-1H-imidazol-3-ium
1,3-bis[(5S)-5-amino-5-carboxypentyl]-5-methyl-1H-imidazol-3-ium
Synonyms Sources
imidazolysine ChEBI
MOLD ChEBI
Citations Waiting for Citations Types Sources
10487968 PubMed citation Europe PMC
9506998 PubMed citation Europe PMC
Last Modified
16 December 2014
General Comment
2011-01-26 A Maillard reaction-derived protein crosslink in the human lens which may a role in lens aging and cataractogenesis.