glucosepane

Glucosepane is a lysine-arginine protein cross-linking product and advanced glycation end product (AGE) derived from D-glucose. It is an irreversible, covalent cross-link product that has been found to make intermolecular and intramolecular cross-links in the collagen of the extracellular matrix (ECM) and crystallin of the eyes. Covalent protein cross-links irreversibly link proteins together in the ECM of tissues. Glucosepane is present in human tissues at levels 10 to 1000 times higher than any other cross-linking AGE, and is currently considered to be the most important cross-linking AGE.

In the Vinony graph

Vinony's link graph records 2 inbound references to glucosepane, and connects out to Amadori rearrangement, protein and diabetes.

It is catalogued under topics including Chembox image size set and Post-translational modification.

Vinony links it to 6 Wikipedia language editions.

Chemical data

Formula: C18H32N6O6
Molecular weight: 428.5 g/mol
IUPAC name: (2S)-2-amino-6-[(6R,7S)-2-[[(4S)-4-amino-4-carboxybutyl]amino]-6,7-dihydroxy-6,7,8,8a-tetrahydro-5H-imidazo[4,5-b]azepin-4-yl]hexanoic acid
SMILES: C1[C@@H]([C@@H](CN(C2=NC(=NC21)NCCC[C@@H](C(=O)O)N)CCCC[C@@H](C(=O)O)N)O)O
InChIKey: JTMICRULXGWYCN-WSOGJNRSSA-N
XLogP: -7.2
Polar surface area: 207 Å²
H-bond donors: 7
H-bond acceptors: 9
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: chemical compound
Has part: hydrogen
Mass: 428.23833274399993

Show 4 more facts

canonical SMILES: C1C(C(CN(C2=NC(=NC12)NCCCC(C(=O)O[H])N)CCCCC(C(=O)O[H])N)O[H])O[H]
density: 1.6
chemical formula: C₁₈H₃₂N₆O₆
isomeric SMILES: N[C@@H](CCCCN1C[C@@H](O)[C@@H](O)CC2NC(=NCCC[C@H](N)C(=O)O)N=C21)C(=O)O

Sources (2)

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