1.0 2011-09-21 00:26:58 UTC 2015-07-21 06:57:36 UTC FDB023252 Pentosidine Pentosidine is a carbohydrate-derived advanced glycation end products (AGEs) that is considerably elevated in uremic patients. Derived from ribose, a pentose, pentosidine forms fluorescent cross-links between the arginine and lysine residues in collagen. It is formed in a reaction of the amino acids with the Maillard reaction products of ribose. Although it is present only in trace concentrations among tissue proteins, it is useful for assessing cumulative damage to proteins-advanced glycation endproductsThis compound per se has no biological activities but is highly correlated to the levels of precursors of carbonyl compounds, and for this reason is considered a reliable surrogate marker for AGEs. The modification of proteins in uremia is not limited to AGEs, since advanced lipoxidation end products are also demonstrable in plasma proteins in uremia. The accumulation of these compounds does not seem to be dependent only on the decline of renal function. Carbonyl precursors of AGEs and advanced lipoxidation end products are markedly elevated in uremic patients. Preliminary cross-sectional studies in haemodialysis patients seem to indicate that the AGEs and carbonyl stress may be involved in the pathogenesis of alterations in left ventricular geometry and function in these patients. (PMID 11051031) The plasma pentosidine level in diabetic nephropathy was found to be determined by factors such as renal function control of glucose and the patient's age; of these, renal function was the most critical factor. The pathological role of AGEs in diabetic nephropathy, is in the expanded mesangial area of diffuse diabetic glomerulosclerosis, with nodular lesions, characteristic of diabetic nephropathy. These suggests a potential link of AGEs accumulation, which may be determined by renal function, control of glucose and age, to renal tissue damage in diabetic nephropathy. (PMID 9044316) The rate of accumulation of glycoxidation products is accelerated in diabetes and age-adjusted concentrations of two advanced glycation end-products (AGE) in tissue proteins, N(6)-carboxymethyllysine and pentosidine, correlate with the severity of complication in diabetic patients. (PMID 9044306) [HMDB] pentosidine C17H26N6O4 378.4261 378.20155335 (2S)-2-amino-6-(2-{[(4S)-4-amino-4-carboxybutyl]amino}-4H-imidazo[4,5-b]pyridin-4-yl)hexanoic acid pentosidine 124505-87-9 N[C@@H](CCCCN1C=CC=C2N=C(NCCC[C@H](N)C(O)=O)N=C12)C(O)=O 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 AYEKKSTZQYEZPU-RYUDHWBXSA-N belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-alpha-amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic heteropolycyclic compounds Amino acids Amino fatty acids Azacyclic compounds Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Heteroaromatic compounds Heterocyclic fatty acids Hydrocarbon derivatives Imidazoles Imidazopyridines Medium-chain fatty acids Monoalkylamines Organic oxides Organopnictogen compounds Pyridines and derivatives Amine Amino acid Amino fatty acid Aromatic heteropolycyclic compound Azacycle Azole Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Fatty acid Fatty acyl Heteroaromatic compound Heterocyclic fatty acid Hydrocarbon derivative Imidazole Imidazopyridine L-alpha-amino acid Medium-chain fatty acid Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Pyridine imidazopyridine non-proteinogenic L-alpha-amino acid Solid logp -3.73 ALOGPS logs -3.34 ALOGPS solubility 1.73e-01 g/l ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 1.51 ChemAxon pka_strongest_basic 9.83 ChemAxon iupac (2S)-2-amino-6-(2-{[(4S)-4-amino-4-carboxybutyl]amino}-4H-imidazo[4,5-b]pyridin-4-yl)hexanoic acid ChemAxon average_mass 378.4261 ChemAxon mono_mass 378.20155335 ChemAxon smiles N[C@@H](CCCCN1C=CC=C2N=C(NCCC[C@H](N)C(O)=O)N=C12)C(O)=O ChemAxon formula C17H26N6O4 ChemAxon 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 ChemAxon inchikey AYEKKSTZQYEZPU-RYUDHWBXSA-N ChemAxon polar_surface_area 169.38 ChemAxon refractivity 99.61 ChemAxon polarizability 40.55 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 15413 Specdb::CMs 38674 Specdb::CMs 136739 Specdb::CMs 144473 Specdb::NmrOneD 34962 Specdb::NmrOneD 34963 Specdb::NmrOneD 34964 Specdb::NmrOneD 34965 Specdb::NmrOneD 34966 Specdb::NmrOneD 34967 Specdb::NmrOneD 34968 Specdb::NmrOneD 34969 Specdb::NmrOneD 34970 Specdb::NmrOneD 34971 Specdb::NmrOneD 34972 Specdb::NmrOneD 34973 Specdb::NmrOneD 34974 Specdb::NmrOneD 34975 Specdb::NmrOneD 34976 Specdb::NmrOneD 34977 Specdb::NmrOneD 34978 Specdb::NmrOneD 34979 Specdb::NmrOneD 34980 Specdb::NmrOneD 34981 Specdb::MsMs 87852 Specdb::MsMs 87853 Specdb::MsMs 87854 Specdb::MsMs 150453 Specdb::MsMs 150454 Specdb::MsMs 150455 Specdb::MsMs 2769359 Specdb::MsMs 2769360 Specdb::MsMs 2769361 Specdb::MsMs 2912945 Specdb::MsMs 2912946 Specdb::MsMs 2912947 HMDB03933 #<Reference:0x000055ce335c8418> #<Reference:0x000055ce335c8260> #<Reference:0x000055ce335c8080> #<Reference:0x00007f093c1afe90> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823