1.0 2011-09-21 00:25:22 UTC 2019-11-26 03:21:07 UTC FDB023148 D-Glutamic acid There are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid, is not endogenously produced in higher mammals. It is found naturally primarily in the cell walls of certain bacteria. D-glutamate is also present in certain foods e.g., soybeans and also arises from the turnover of the intestinal tract microflora, whose cell walls contain significant D-glutamate. Unlike other D-amino acids, D-glutamate is not oxidized by the D-amino acid oxidases, and therefore this detoxification pathway is not available for handling D-glutamate. Likewise, D-glutamic acid, when ingested, largely escapes most deamination reactions (unlike the L-counterpart). Free D-glutamate is found in mammalian tissue at surprisingly high levels, with D-glutamate accounting for 9% of the total glutamate present in liver. D-glutamate is the most potent natural inhibitor of glutathione synthesis identified to date and this may account for its localization to the liver, since circulating D-glutamate may alter redox stabiity (PMID 11158923). Certain eels are known to use D-glutamic acid as a phermone for chemical communication. [HMDB] (2R)-2-aminopentanedioate (2R)-2-aminopentanedioic acid (R)-2-aminopentanedioate (R)-2-aminopentanedioic acid D-2-Aminoglutarate D-2-Aminoglutaric acid D-2-Aminopentanedioate D-2-Aminopentanedioic acid D-Glutamate D-Glutamic acid D-Glutaminate D-Glutaminic acid D-Glutaminsaeure delta-2-Aminoglutarate delta-2-Aminoglutaric acid delta-2-Aminopentanedioate delta-2-Aminopentanedioic acid delta-Glutamate delta-Glutamic acid delta-Glutaminate delta-Glutaminic acid delta-Glutaminsaeure DGL glutamic acid D-form Lopac-G-2128 Lopac-gamma-2128 R-(-)-Glutamate R-(-)-Glutamic acid Tocris-0217 C5H9NO4 147.1293 147.053157781 (2R)-2-aminopentanedioic acid D-glutamic acid 6893-26-1 N[C@H](CCC(O)=O)C(O)=O InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m1/s1 WHUUTDBJXJRKMK-GSVOUGTGSA-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 Amino fatty acids Carbonyl compounds Carboxylic acids D-alpha-amino acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Amino fatty acid Carbonyl group Carboxylic acid D-alpha-amino acid Dicarboxylic acid or derivatives Fatty acid Fatty acyl Glutamic acid or derivatives Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine D-alpha-amino acid Other amino acids glutamic acid logp -3.54 ALOGPS logs -0.26 ALOGPS solubility 8.06e+01 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 1.88 ChemAxon pka_strongest_basic 9.54 ChemAxon iupac (2R)-2-aminopentanedioic acid ChemAxon average_mass 147.1293 ChemAxon mono_mass 147.053157781 ChemAxon smiles N[C@H](CCC(O)=O)C(O)=O ChemAxon formula C5H9NO4 ChemAxon inchi InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m1/s1 ChemAxon inchikey WHUUTDBJXJRKMK-GSVOUGTGSA-N ChemAxon polar_surface_area 100.62 ChemAxon refractivity 31.29 ChemAxon polarizability 13.19 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 135650 Specdb::NmrOneD 135651 Specdb::NmrOneD 135652 Specdb::NmrOneD 135653 Specdb::NmrOneD 135654 Specdb::NmrOneD 135655 Specdb::NmrOneD 135656 Specdb::NmrOneD 135657 Specdb::NmrOneD 135658 Specdb::NmrOneD 135659 Specdb::NmrOneD 135660 Specdb::NmrOneD 135661 Specdb::NmrOneD 135662 Specdb::NmrOneD 135663 Specdb::NmrOneD 135664 Specdb::NmrOneD 135665 Specdb::NmrOneD 135666 Specdb::NmrOneD 135667 Specdb::NmrOneD 135668 Specdb::NmrOneD 135669 Specdb::CMs 9441 Specdb::CMs 38576 Specdb::CMs 137814 Specdb::CMs 145548 Specdb::MsMs 25412 Specdb::MsMs 25413 Specdb::MsMs 25414 Specdb::MsMs 31970 Specdb::MsMs 31971 Specdb::MsMs 31972 Specdb::MsMs 437667 Specdb::MsMs 437668 Specdb::MsMs 437669 Specdb::MsMs 437670 Specdb::MsMs 437671 Specdb::MsMs 446166 Specdb::MsMs 446167 Specdb::MsMs 446168 Specdb::MsMs 446169 Specdb::MsMs 446170 Specdb::MsMs 2821188 Specdb::MsMs 2821189 Specdb::MsMs 2821190 Specdb::MsMs 2857002 Specdb::MsMs 2857003 Specdb::MsMs 2857004 HMDB03339 15966 Cow milk, pasteurized, vitamin A + D added, 0% fat Type 2 specific Cow milk, pasteurized, vitamin A + D added, 1% fat Type 2 specific Cow milk, pasteurized, vitamin A + D added, 2% fat Type 2 specific Cow milk, pasteurized, vitamin D added, 3.25% fat Type 2 specific