CHEBI:59951 - pentosidine

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ChEBI Name pentosidine
ChEBI ID CHEBI:59951
Definition An imidazopyridine having norleucine and ornithine residues attached via their side-chains at the 4- and 2-positions respectively.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C17H26N6O4
Net Charge 0
Average Mass 378.42610
Monoisotopic Mass 378.20155
InChI InChI=1S/C17H26N6O4/c18-11(15(24)25)5-1-2-9-23-10-4-7-13-14(23)22-17(21-13)20-8-3-6-12(19)16(26)27/h4,7,10-12H,1-3,5-6,8-9,18-19H2,(H,20,21)(H,24,25)(H,26,27)/t11-,12-/m0/s1
InChIKey AYEKKSTZQYEZPU-RYUDHWBXSA-N
SMILES N[C@@H](CCCCn1cccc2nc(NCCC[C@H](N)C(O)=O)nc12)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 )
Application(s): cross-linking reagent
A reagent with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between macromolecules, principally side chains of amino acids in proteins, allowing the locations of naturally reactive areas within the proteins to be identified.
biomarker
A substance used as an indicator of a biological state.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing pentosidine (CHEBI:59951) has role biomarker (CHEBI:59163)
pentosidine (CHEBI:59951) has role cross-linking reagent (CHEBI:50684)
pentosidine (CHEBI:59951) is a imidazopyridine (CHEBI:46908)
pentosidine (CHEBI:59951) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
IUPAC Name
6-(2-{[(4S)-4-amino-4-carboxybutyl]amino}-4H-imidazo[4,5-b]pyridin-4-yl)-L-norleucine
Registry Numbers Types Sources
124505-87-9 CAS Registry Number ChemIDplus
9298644 Beilstein Registry Number Beilstein
9298644 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18448811 PubMed citation Europe PMC
19120887 PubMed citation Europe PMC
8070089 PubMed citation Europe PMC
Last Modified
23 October 2015
General Comment
2010-12-18 Pentosidine is an advanced glycation end-product (AGE) with demonstrated involvement in ulcerative colitis and age-related bone mass loss.