1.0 2011-09-21 00:13:31 UTC 2015-10-09 22:33:01 UTC FDB022406 N-Acetylaspartylglutamic acid N-Acetylaspartylglutamate (NAAG) is a neuropeptide found in millimolar concentrations in brain that is localized to subpopulations of glutamatergic, cholinergic, GABAergic, and noradrenergic neuronal systems. NAAG is released upon depolarization by a Ca(2+)-dependent process and is an agonist at mGluR3 receptors and an antagonist at NMDA receptors. NAAG is catabolized to N-acetylaspartate and glutamate primarily by glutamate carboxypeptidase II, which is expressed on the extracellular surface of astrocytes. The levels of NAAG and the activity of carboxypeptidase II are altered in a regionally specific fashion in several neuropsychiatric disorders. (PMID 9361299) N-Acetylaspartylglutamic acid (NAAG) is a purported precursor of N-Acetylaspartic acid (NAA) and is present at about one-tenth of the concentration of NAA in the brain. NAAG has been reported to activate N-methyl- D-aspartic acid (NMDA) receptors in neurons. Previous immunohistochemical studies in the vertebrate central nervous system (CNS) have suggested that NAAG is exclusively localized to neurons. Recent evidence, however, indicates that NAAG might also be localized to nonneuronal cells within the CNS. Only traces of NAA and NAAG are detectable in other tissues. Some compounds can change levels of NAA and NAAG in the brain. For example, methylphenidante increases the levels of NAA and NAAG in the cerebral cortex; amphetamine also increases NAA concentration in a mature brain by 26%, raising the possibility that other neurochemical systems might be involved in the clinical effects of stimulants. (PMID: 10603234) [HMDB] a-Spaglumic acid Acetyl-a-L-aspartylglutamic acid Acetyl-alpha-L-aspartylglutamic acid alpha-Spaglumic acid Isospaglumic acid N-(N-Acetylaspartyl)glutamic acid N-Acetyl-a-aspartylglutamic acid N-Acetyl-a-L-aspartyl-L-glutamic acid N-Acetyl-alpha-aspartylglutamic acid N-Acetyl-alpha-L-aspartyl-L-glutamic acid N-Acetyl-L-aspartyl-L-glutamic acid NAAG C11H16N2O8 304.2533 304.090665498 2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid 2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid 3106-85-2 CC(=O)NC(CC(O)=O)C(=O)NC(CCC(O)=O)C(O)=O InChI=1S/C11H16N2O8/c1-5(14)12-7(4-9(17)18)10(19)13-6(11(20)21)2-3-8(15)16/h6-7H,2-4H2,1H3,(H,12,14)(H,13,19)(H,15,16)(H,17,18)(H,20,21) OPVPGKGADVGKTG-UHFFFAOYSA-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 Acetamides Alpha amino acid amides Aspartic acid and derivatives Carbonyl compounds Carboxylic acids Glutamic acid and derivatives Hydrocarbon derivatives N-acyl amines N-acyl-alpha amino acids Organic oxides Organonitrogen compounds Organopnictogen compounds Secondary carboxylic acid amides Tricarboxylic acids and derivatives Acetamide Aliphatic acyclic compound Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-dipeptide Aspartic acid or derivatives Carbonyl group Carboxamide group Carboxylic acid Fatty acyl Fatty amide Glutamic acid or derivatives Hydrocarbon derivative N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine N-substituted-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Secondary carboxylic acid amide Tricarboxylic acid or derivatives Solid logp -1.10 ALOGPS logs -1.97 ALOGPS solubility 3.29e+00 g/l ALOGPS logp -2.3 ChemAxon pka_strongest_acidic 3.13 ChemAxon pka_strongest_basic -2 ChemAxon iupac 2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid ChemAxon average_mass 304.2533 ChemAxon mono_mass 304.090665498 ChemAxon smiles CC(=O)NC(CC(O)=O)C(=O)NC(CCC(O)=O)C(O)=O ChemAxon formula C11H16N2O8 ChemAxon inchi InChI=1S/C11H16N2O8/c1-5(14)12-7(4-9(17)18)10(19)13-6(11(20)21)2-3-8(15)16/h6-7H,2-4H2,1H3,(H,12,14)(H,13,19)(H,15,16)(H,17,18)(H,20,21) ChemAxon inchikey OPVPGKGADVGKTG-UHFFFAOYSA-N ChemAxon polar_surface_area 170.1 ChemAxon refractivity 64.06 ChemAxon polarizability 27 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1581 Specdb::MsMs 1412 Specdb::MsMs 1413 Specdb::MsMs 1414 Specdb::MsMs 318127 Specdb::MsMs 318128 Specdb::MsMs 318129 Specdb::MsMs 364819 Specdb::MsMs 364820 Specdb::MsMs 364821 Specdb::CMs 23522 Specdb::CMs 37914 Specdb::CMs 121325 Specdb::CMs 945845 Specdb::CMs 945846 Specdb::CMs 945847 Specdb::CMs 945848 Specdb::CMs 945849 Specdb::CMs 945850 Specdb::CMs 945851 Specdb::CMs 945852 Specdb::CMs 945853 Specdb::CMs 945854 Specdb::CMs 945855 Specdb::CMs 945856 Specdb::CMs 945857 Specdb::CMs 945858 Specdb::CMs 945859 Specdb::CMs 945860 Specdb::CMs 945861 Specdb::CMs 945862 Specdb::CMs 945863 Specdb::CMs 945864 Specdb::CMs 945865 Specdb::CMs 945866 Specdb::NmrOneD 1640 Specdb::NmrOneD 226397 Specdb::NmrOneD 226398 Specdb::NmrOneD 226399 Specdb::NmrOneD 226400 Specdb::NmrOneD 226401 Specdb::NmrOneD 226402 Specdb::NmrOneD 226403 Specdb::NmrOneD 226404 Specdb::NmrOneD 226405 Specdb::NmrOneD 226406 Specdb::NmrOneD 226407 Specdb::NmrOneD 226408 Specdb::NmrOneD 226409 Specdb::NmrOneD 226410 Specdb::NmrOneD 226411 Specdb::NmrOneD 226412 Specdb::NmrOneD 226413 Specdb::NmrOneD 226414 Specdb::NmrOneD 226415 Specdb::NmrOneD 226416 HMDB01067 #<Reference:0x000055ce327b6f50> #<Reference:0x000055ce327b6d98> 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