1.0 2011-09-21 00:35:54 UTC 2015-07-21 06:57:54 UTC FDB023860 5-L-Glutamyl-L-alanine 5-L-Glutamyl-L-alanine is a natural substrate of the enzyme 5-L-glutamyl)-L-amino acid 5-glutamyltransferase (cyclizing) (g-glutamylcyclotransferase, EC 2.3.2.2) in the glutathione metabolism pathway, which cleaves 5-L-Glutamyl-L-alanine, producing L-5-oxoproline. gamma-Glutamylcyclotransferase is widely distributed in both human and animal tissues where it catalyzes the scission of the y-peptide bonds of many different gamma-glutamyl-aminoacids and gamma-glutamyl-gamma-glutamyl-amino-acids. The latter are 'better' substrates of the enzyme than the corresponding gamma-glutamyl - amino-acids. (PMID: 2570694, 2893631) [HMDB] 5-L-glutamylalanine g-Gln-ala g-Glu-Ala g-Glutamylalanine g-L-Glutamyl-L-alanine gamma-Gln-ala gamma-Glu-Ala gamma-Glutamylalanine gamma-L-Glutamyl-L-alanine N-L-g-Glutamyl-L-alanine N-L-gamma-Glutamyl-L-alanine N-L-γ-glutamyl-L-alanine γ-gln-ala C8H14N2O5 218.2072 218.090271568 (2S)-2-amino-4-{[(1S)-1-carboxyethyl]carbamoyl}butanoic acid g-glu-ala 5875-41-2 C[C@H](NC(=O)CC[C@H](N)C(O)=O)C(O)=O InChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1 WQXXXVRAFAKQJM-WHFBIAKZSA-N belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Dipeptides Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Alanine and derivatives Amino acids Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Fatty acids and conjugates Gamma-glutamyl amino acids Glutamine and derivatives Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines N-acyl amines N-acyl-L-alpha-amino acids Organic oxides Organopnictogen compounds Secondary carboxylic acid amides Alanine or derivatives Aliphatic acyclic compound Alpha-amino acid Alpha-amino acid or derivatives Alpha-dipeptide Amine Amino acid Amino acid or derivatives Carbonyl group Carboxamide group Carboxylic acid Dicarboxylic acid or derivatives Fatty acid Fatty acyl Fatty amide Gamma-glutamyl alpha-amino acid Glutamine or derivatives Hydrocarbon derivative L-alpha-amino acid N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine N-acyl-l-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Secondary carboxylic acid amide gamma-glutamylalanine Solid logp -3.36 ALOGPS logs -1.23 ALOGPS solubility 1.29e+01 g/l ALOGPS logp -3.8 ChemAxon pka_strongest_acidic 1.93 ChemAxon pka_strongest_basic 9.31 ChemAxon iupac (2S)-2-amino-4-{[(1S)-1-carboxyethyl]carbamoyl}butanoic acid ChemAxon average_mass 218.2072 ChemAxon mono_mass 218.090271568 ChemAxon smiles C[C@H](NC(=O)CC[C@H](N)C(O)=O)C(O)=O ChemAxon formula C8H14N2O5 ChemAxon inchi InChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1 ChemAxon inchikey WQXXXVRAFAKQJM-WHFBIAKZSA-N ChemAxon polar_surface_area 129.72 ChemAxon refractivity 48.59 ChemAxon polarizability 20.94 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 2476 Specdb::CMs 38981 Specdb::CMs 135581 Specdb::CMs 143315 Specdb::NmrOneD 67992 Specdb::NmrOneD 67993 Specdb::NmrOneD 67994 Specdb::NmrOneD 67995 Specdb::NmrOneD 67996 Specdb::NmrOneD 67997 Specdb::NmrOneD 67998 Specdb::NmrOneD 67999 Specdb::NmrOneD 68000 Specdb::NmrOneD 68001 Specdb::NmrOneD 68002 Specdb::NmrOneD 68003 Specdb::NmrOneD 68004 Specdb::NmrOneD 68005 Specdb::NmrOneD 68006 Specdb::NmrOneD 68007 Specdb::NmrOneD 68008 Specdb::NmrOneD 68009 Specdb::NmrOneD 68010 Specdb::NmrOneD 68011 Specdb::MsMs 178242 Specdb::MsMs 178243 Specdb::MsMs 178244 Specdb::MsMs 180558 Specdb::MsMs 180559 Specdb::MsMs 180560 Specdb::MsMs 2378062 Specdb::MsMs 2378063 Specdb::MsMs 2378064 Specdb::MsMs 2557332 Specdb::MsMs 2557333 Specdb::MsMs 2557334 HMDB06248 #<Reference:0x000055ce323e31a8> #<Reference:0x000055ce323e2ff0> 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