glyoxal-lysine dimer (CHEBI:59965)

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ChEBI Name	glyoxal-lysine dimer

ChEBI ID	CHEBI:59965

Definition	An imidazolium ion formed via cyclo-dimerisation of L-lysine and glyoxal.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C15H27N4O4

Net Charge

Average Mass

327.39930

Monoisotopic Mass

327.20268

InChI

InChI=1S/C15H26N4O4/c16-12(14(20)21)5-1-3-7-18-9-10-19(11-18)8-4-2-6-13(17)15(22)23/h9-13H,1-8,16-17H2,(H-,20,21,22,23)/p+1/t12-,13-/m0/s1

InChIKey

MOISNZWLLXDVFT-STQMWFEESA-O

SMILES

N[C@@H](CCCCn1cc[n+](CCCC[C@H](N)C(O)=O)c1)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.

ChEBI Ontology
Outgoing	glyoxal-lysine dimer (CHEBI:59965) has role epitope (CHEBI:53000) glyoxal-lysine dimer (CHEBI:59965) is a L-lysine derivative (CHEBI:25095) glyoxal-lysine dimer (CHEBI:59965) is a imidazolium ion (CHEBI:59964) glyoxal-lysine dimer (CHEBI:59965) is a non-proteinogenic L-α-amino acid (CHEBI:83822)

IUPAC Name

1,3-bis[(5S)-5-amino-5-carboxypentyl]-1H-imidazol-3-ium

Synonym	Source
GOLD	ChEBI

Last Modified

16 December 2014

General Comment
2010-12-14	Implicated in the formation of advanced glycation end-products (AGEs), a feature of hyperglycaemia and aging.