1.0 2011-09-21 01:39:26 UTC 2015-07-21 06:59:24 UTC FDB028415 gamma-Glutamylglutamic acid gammaGlutamylglutamic acid is made of two glutamic acid molecules. Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid) [HMDB] (5-L-Glutamyl)-L-glutamate (5-L-Glutamyl)-L-glutamic acid g-Glutamylglutamate g-Glutamylglutamic acid g-L-Glu-L-glu gamma-Glutamylglutamate gamma-L-Glu-L-glu N-gamma-L-Glutamyl-L-glutamic acid γ-glutamylglutamate γ-glutamylglutamic acid γ-L-glu-L-glu C10H16N2O7 276.2432 276.095750876 (2S)-2-[(4S)-4-amino-4-carboxybutanamido]pentanedioic acid (2S)-2-[(4S)-4-amino-4-carboxybutanamido]pentanedioic acid 1116-22-9 N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O InChI=1S/C10H16N2O7/c11-5(9(16)17)1-3-7(13)12-6(10(18)19)2-4-8(14)15/h5-6H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)(H,18,19)/t5-,6-/m0/s1 OWQDWQKWSLFFFR-WDSKDSINSA-N belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Glutamic acid and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboximidic acids Carboxylic acids Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Tricarboxylic acids and derivatives Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Carbonyl group Carboximidic acid Carboximidic acid derivative Carboxylic acid Glutamic acid or derivatives Hydrocarbon derivative L-alpha-amino acid N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Propargyl-type 1,3-dipolar organic compound Tricarboxylic acid or derivatives dipeptide Solid logp -3.19 ALOGPS logs -1.55 ALOGPS solubility 7.75e+00 g/l ALOGPS logp -4.2 ChemAxon pka_strongest_acidic 1.93 ChemAxon pka_strongest_basic 9.31 ChemAxon iupac (2S)-2-[(4S)-4-amino-4-carboxybutanamido]pentanedioic acid ChemAxon average_mass 276.2432 ChemAxon mono_mass 276.095750876 ChemAxon smiles N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O ChemAxon formula C10H16N2O7 ChemAxon inchi InChI=1S/C10H16N2O7/c11-5(9(16)17)1-3-7(13)12-6(10(18)19)2-4-8(14)15/h5-6H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)(H,18,19)/t5-,6-/m0/s1 ChemAxon inchikey OWQDWQKWSLFFFR-WDSKDSINSA-N ChemAxon polar_surface_area 167.02 ChemAxon refractivity 59.38 ChemAxon polarizability 25.7 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 14568 Specdb::CMs 39786 Specdb::CMs 134422 Specdb::CMs 142156 Specdb::MsMs 298201 Specdb::MsMs 298202 Specdb::MsMs 298203 Specdb::MsMs 339922 Specdb::MsMs 339923 Specdb::MsMs 339924 Specdb::MsMs 2318744 Specdb::MsMs 2318745 Specdb::MsMs 2318746 Specdb::MsMs 2617136 Specdb::MsMs 2617137 Specdb::MsMs 2617138 Specdb::NmrOneD 94372 Specdb::NmrOneD 94373 Specdb::NmrOneD 94374 Specdb::NmrOneD 94375 Specdb::NmrOneD 94376 Specdb::NmrOneD 94377 Specdb::NmrOneD 94378 Specdb::NmrOneD 94379 Specdb::NmrOneD 94380 Specdb::NmrOneD 94381 Specdb::NmrOneD 94382 Specdb::NmrOneD 94383 Specdb::NmrOneD 94384 Specdb::NmrOneD 94385 Specdb::NmrOneD 94386 Specdb::NmrOneD 94387 Specdb::NmrOneD 94388 Specdb::NmrOneD 94389 Specdb::NmrOneD 94390 Specdb::NmrOneD 94391 HMDB11737 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