1.0 2016-10-03 18:24:02 UTC 2021-01-12 22:02:01 UTC BMDB0011753 BMDB11753 Iminodiacetate Iminodiacetic acid (IDA) is a dicarboxylic acid amine. It is a strongly acidic compound that is very water soluble. It naturally exists as a white powder. IDA is food by-product or intermediate produced via the reaction of glycine with acrylamide through the heating, baking or frying of carbohydrate-rich foods such as potatoes (PMID: 25212154).  Acrylamide is typically produced through a Maillard reaction (a heating reaction) of asparagine and various reducing sugars in plant-derived foods (PMID: 12368844). Concentrations of IDA are reduced in the plasma of individuals with autism (PMID: 33087514) and elevated in individuals with acute respiratory distress syndrome (ARDS) (PMID: 30779905). In addition to its role in metabolism, IDA has many industrial applications or roles. For instance, it is an important intermediate in the manufacture the herbicide glyphosate. IDA is also used in capillary electrophoresis for modulating peptide mobility and can be used as a precursor for the manufacture of the indicator xylenol orange. The iminodiacetate anion can act as a tridentate ligand to form a metal complex with two, fused, five membered chelate rings. The proton on the nitrogen atom can be replaced by a carbon atom of a polymer to create an ion-exchange resin, such as chelex 100. Iminodiacetic acid is used in HIDA (hepatobiliary iminodiacetic acid) scans or cholescintigraphy scans, that employ the radionuclide Technetium 99m, to diagnose several diseases in the liver, gallbladder and bile duct. 2,2'-Azanediyldiacetic acid 2-[(Carboxymethyl)amino]acetic acid Aminodiacetic acid Bis(carboxymethyl)amine Diglycine Diglycocoll IDA Iminobis(acetic acid) Iminodiethanoic acid N-(Carboxymethyl)glycine 2,2'-Azanediyldiacetate 2-[(Carboxymethyl)amino]acetate Aminodiacetate Iminobis(acetate) Iminodiethanoate Iminodiacetate Imidodiacetic acid Iminodiacetic acid, disodium salt Iminodiacetic acid, calcium salt (1:1) Iminodiacetic acid, sodium salt 2,2'-Iminodiacetic acid 2,2'-Iminodiacetate N-(Carboxymethyl)- glycine Iminodiacetic acid C4H7NO4 133.1027 133.037507717 2-[(carboxymethyl)amino]acetic acid iminodiacetic acid 142-73-4 OC(=O)CNCC(O)=O InChI=1S/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9) NBZBKCUXIYYUSX-UHFFFAOYSA-N belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Alpha amino acids Amino acids Carbonyl compounds Carboxylic acids Dialkylamines Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Secondary aliphatic amine Secondary amine Aliphatic acyclic compounds amino dicarboxylic acid glycine derivative non-proteinogenic alpha-amino acid Solid logp -2.50 ALOGPS logs -0.56 ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 2.12 ChemAxon pka_strongest_basic 8.8 ChemAxon iupac 2-[(carboxymethyl)amino]acetic acid ChemAxon average_mass 133.1027 ChemAxon mono_mass 133.037507717 ChemAxon smiles OC(=O)CNCC(O)=O ChemAxon formula C4H7NO4 ChemAxon inchi InChI=1S/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9) ChemAxon inchikey NBZBKCUXIYYUSX-UHFFFAOYSA-N ChemAxon polar_surface_area 86.63 ChemAxon refractivity 26.86 ChemAxon polarizability 11.63 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsIr 2613 Specdb::MsIr 2614 Specdb::MsIr 2615 Specdb::CMs 1150 Specdb::CMs 1201 Specdb::CMs 17506 Specdb::CMs 31558 Specdb::CMs 31559 Specdb::CMs 31966 Specdb::CMs 39795 Specdb::CMs 173978 Specdb::MsMs 79059 Specdb::MsMs 79060 Specdb::MsMs 79061 Specdb::MsMs 139560 Specdb::MsMs 139561 Specdb::MsMs 139562 Specdb::MsMs 2798078 Specdb::MsMs 2798079 Specdb::MsMs 2798080 Specdb::MsMs 2881238 Specdb::MsMs 2881239 Specdb::MsMs 2881240 Specdb::NmrOneD 94532 Specdb::NmrOneD 94533 Specdb::NmrOneD 94534 Specdb::NmrOneD 94535 Specdb::NmrOneD 94536 Specdb::NmrOneD 94537 Specdb::NmrOneD 94538 Specdb::NmrOneD 94539 Specdb::NmrOneD 94540 Specdb::NmrOneD 94541 Specdb::NmrOneD 94542 Specdb::NmrOneD 94543 Specdb::NmrOneD 94544 Specdb::NmrOneD 94545 Specdb::NmrOneD 94546 Specdb::NmrOneD 94547 Specdb::NmrOneD 94548 Specdb::NmrOneD 94549 Specdb::NmrOneD 94550 Specdb::NmrOneD 94551 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 FDB028424 8557 C19911 8897 24786 C00053341 CPD-10189 Iminodiacetic_acid Liu J, Chen F, Man Y, Dong J, Hu X: The pathways for the removal of acrylamide in model systems using glycine based on the identification of reaction products. Food Chem. 2011 Sep 15;128(2):442-9. doi: 10.1016/j.foodchem.2011.03.051. Epub 2011 Mar 12. 25212154 Mottram DS, Wedzicha BL, Dodson AT: Acrylamide is formed in the Maillard reaction. Nature. 2002 Oct 3;419(6906):448-9. doi: 10.1038/419448a. 12368844 Kang DW, Adams JB, Vargason T, Santiago M, Hahn J, Krajmalnik-Brown R: Distinct Fecal and Plasma Metabolites in Children with Autism Spectrum Disorders and Their Modulation after Microbiota Transfer Therapy. mSphere. 2020 Oct 21;5(5). pii: 5/5/e00314-20. doi: 10.1128/mSphere.00314-20. 33087514 Lin S, Yue X, Wu H, Han TL, Zhu J, Wang C, Lei M, Zhang M, Liu Q, Xu F: Explore potential plasma biomarkers of acute respiratory distress syndrome (ARDS) using GC-MS metabolomics analysis. Clin Biochem. 2019 Apr;66:49-56. doi: 10.1016/j.clinbiochem.2019.02.009. Epub 2019 Feb 16. 30779905