Showing metabocard for Iminodiacetate (BMDB0011753)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:24:02 UTC
Update Date2021-01-12 22:02:01 UTC
BMDB IDBMDB0011753
Secondary Accession Numbers
  • BMDB11753
Metabolite Identification
Common NameIminodiacetate
DescriptionIminodiacetic 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.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2,2'-Azanediyldiacetic acidChEBI
2-[(Carboxymethyl)amino]acetic acidChEBI
Aminodiacetic acidChEBI
Bis(carboxymethyl)amineChEBI
DiglycineChEBI
DiglycocollChEBI
IDAChEBI
Iminobis(acetic acid)ChEBI
Iminodiethanoic acidChEBI
N-(Carboxymethyl)glycineChEBI
2,2'-AzanediyldiacetateGenerator
2-[(Carboxymethyl)amino]acetateGenerator
AminodiacetateGenerator
Iminobis(acetate)Generator
IminodiethanoateGenerator
IminodiacetateGenerator
Imidodiacetic acidMeSH
Iminodiacetic acid, disodium saltMeSH
Iminodiacetic acid, calcium salt (1:1)MeSH
Iminodiacetic acid, sodium saltMeSH
2,2'-Iminodiacetic acidChEBI
2,2'-IminodiacetateGenerator
N-(Carboxymethyl)- glycineHMDB
Iminodiacetic acidGenerator
Chemical FormulaC4H7NO4
Average Molecular Weight133.1027
Monoisotopic Molecular Weight133.037507717
IUPAC Name2-[(carboxymethyl)amino]acetic acid
Traditional Nameiminodiacetic acid
CAS Registry Number142-73-4
SMILES
OC(=O)CNCC(O)=O
InChI Identifier
InChI=1S/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9)
InChI KeyNBZBKCUXIYYUSX-UHFFFAOYSA-N
Chemical Taxonomy
Description 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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Secondary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.5ALOGPS
logP-4.1ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)2.12ChemAxon
pKa (Strongest Basic)8.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity26.86 m³·mol⁻¹ChemAxon
Polarizability11.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03dl-1900000000-bc536bd33b5bb4d504f1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-5980000000-f8e3bf4eb6a737036f63View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03dl-1900000000-bc536bd33b5bb4d504f1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-5980000000-f8e3bf4eb6a737036f63View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-1960000000-42f0b8b3958f9e85b38fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9100000000-451fcc1fe69f887e037cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03k9-9740000000-ce4b506cbc11cc8c9ca4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-6900000000-ce1ff0b0bde548998e5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9300000000-7ffe6ab49ebab30d1c88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-8aa1d405b1000e5ce917View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-0520ac09c2ffb0ca305aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900000000-57e171a290e264d2ca9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0buc-9200000000-dec8a7def44b6da0fc20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9400000000-57ab56c449e819d94318View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9000000000-9b3c69cf26b28b50903aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-7691ad1fbfdd9e569959View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9600000000-3ebb5cf862bee16e9bb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-e0c6b60e6e3064d4c44cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e72dda8bd4f92441e1c6View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Mammary Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0011753
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028424
KNApSAcK IDC00053341
Chemspider ID8557
KEGG Compound IDC19911
BioCyc IDCPD-10189
BiGG IDNot Available
Wikipedia LinkIminodiacetic_acid
METLIN IDNot Available
PubChem Compound8897
PDB IDNot Available
ChEBI ID24786
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:25212154 ]
  2. 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. [PubMed:12368844 ]
  3. 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. [PubMed:33087514 ]
  4. 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. [PubMed:30779905 ]