1.0 2011-09-21 00:26:46 UTC 2015-07-21 06:57:36 UTC FDB023239 Epsilon-(gamma-Glutamyl)-lysine In non-diabetic kidney scarring the protein crosslinking enzyme tissue transglutaminase (tTg) has been implicated in the process by the formation of increased epsilon-(gamma-glutamyl)lysine bonds between ECM components in both experimental and human disease. Changes in tTg and epsilon-(gamma-glutamyl)lysine occur in human Diabetic nephropathy as well, the leading cause of chronic kidney failure. (PMID 15292688) In Parkinson's disease (PD), conformational changes in the alpha-synuclein monomer precede the formation of Lewy bodies. Both tTG and its substrate-characteristic N(epsilon)-(gamma-glutamyl)-lysine crosslink are increased in PD nigral dopamine neurons. (PMID 15001552) Expression of tissue transglutaminase (tTgase) and epsilon-(gamma-glutamyl)-lysine was present in all scarring of the blebs sites, being the main cause of failure in glaucoma filtration surgery. Transglutaminases are calcium-dependent enzymes that catalyze the posttranslational modification of proteins through an acyl transfer reaction between the gamma-carboxamide group of a peptide-bound glutaminyl residue and various amines. Covalent cross-linking using epsilon-(gamma-glutamyl)-lysine bonds is stable and resistant to enzymatic, chemical, and mechanical disruption. (PMID: 16936095) [HMDB] Epsilon-(gamma-glu)-LYS Epsilon-(gamma-glutamyl)-lysine Epsilon-(gamma-glutamyl)lysine Epsilon-(gamma-glutamyl)lysine isodipeptide Epsilon-(gamma-l-glutamyl)-l-lysine N(6)-L-gamma-Glutamyl-L-lysine N(epsilon)-(gamma-glutamyl)-lysine C11H21N3O5 275.3015 275.148120797 (2S)-2-amino-6-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid N(6)-L-gamma-glutamyl-L-lysine 17105-15-6 N[C@@H](CCCCNC(=O)CC[C@H](N)C(O)=O)C(O)=O InChI=1S/C11H21N3O5/c12-7(10(16)17)3-1-2-6-14-9(15)5-4-8(13)11(18)19/h7-8H,1-6,12-13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1 JPKNLFVGUZRHOB-YUMQZZPRSA-N belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Glutamine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Amino fatty acids Carbonyl compounds Carboxylic acid salts Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives L-alpha-amino acids Medium-chain fatty acids Monoalkylamines N-acyl amines Organic oxides Organic salts Organic zwitterions Organopnictogen compounds Secondary carboxylic acid amides Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Amino fatty acid Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid salt Dicarboxylic acid or derivatives Fatty acid Fatty acyl Fatty amide Glutamine or derivatives Hydrocarbon derivative L-alpha-amino acid Medium-chain fatty acid N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organic salt Organic zwitterion Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Secondary carboxylic acid amide Solid logp -3.96 ALOGPS logs -1.81 ALOGPS solubility 4.27e+00 g/l ALOGPS logp -6.1 ChemAxon pka_strongest_acidic 1.94 ChemAxon pka_strongest_basic 9.73 ChemAxon iupac (2S)-2-amino-6-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid ChemAxon average_mass 275.3015 ChemAxon mono_mass 275.148120797 ChemAxon smiles N[C@@H](CCCCNC(=O)CC[C@H](N)C(O)=O)C(O)=O ChemAxon formula C11H21N3O5 ChemAxon inchi InChI=1S/C11H21N3O5/c12-7(10(16)17)3-1-2-6-14-9(15)5-4-8(13)11(18)19/h7-8H,1-6,12-13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1 ChemAxon inchikey JPKNLFVGUZRHOB-YUMQZZPRSA-N ChemAxon polar_surface_area 155.74 ChemAxon refractivity 65.9 ChemAxon polarizability 28.48 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 14758 Specdb::CMs 38664 Specdb::CMs 152401 Specdb::MsMs 298594 Specdb::MsMs 298595 Specdb::MsMs 298596 Specdb::MsMs 340399 Specdb::MsMs 340400 Specdb::MsMs 340401 Specdb::MsMs 2755561 Specdb::MsMs 2755562 Specdb::MsMs 2755563 Specdb::MsMs 2954232 Specdb::MsMs 2954233 Specdb::MsMs 2954234 Specdb::NmrOneD 34842 Specdb::NmrOneD 34843 Specdb::NmrOneD 34844 Specdb::NmrOneD 34845 Specdb::NmrOneD 34846 Specdb::NmrOneD 34847 Specdb::NmrOneD 34848 Specdb::NmrOneD 34849 Specdb::NmrOneD 34850 Specdb::NmrOneD 34851 Specdb::NmrOneD 34852 Specdb::NmrOneD 34853 Specdb::NmrOneD 34854 Specdb::NmrOneD 34855 Specdb::NmrOneD 34856 Specdb::NmrOneD 34857 Specdb::NmrOneD 34858 Specdb::NmrOneD 34859 Specdb::NmrOneD 34860 Specdb::NmrOneD 34861 HMDB03869 #<Reference:0x00007f093c078b58> #<Reference:0x00007f093c0789a0> #<Reference:0x00007f093c0787e8> #<Reference:0x00007f093c078630> 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