Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-03-17 13:28:50 UTC
Update Date2023-02-21 17:17:36 UTC
HMDB IDHMDB0011753
Secondary Accession Numbers
  • HMDB11753
Metabolite Identification
Common NameIminodiacetic acid
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
Data?1676999856
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point247.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point370.56 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility475800 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.840 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility36.9 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.44731661259
DarkChem[M-H]-121.41331661259
DeepCCS[M+H]+126.46930932474
DeepCCS[M-H]-123.66130932474
DeepCCS[M-2H]-160.03630932474
DeepCCS[M+Na]+135.03130932474
AllCCS[M+H]+129.832859911
AllCCS[M+H-H2O]+125.732859911
AllCCS[M+NH4]+133.532859911
AllCCS[M+Na]+134.632859911
AllCCS[M-H]-124.832859911
AllCCS[M+Na-2H]-127.532859911
AllCCS[M+HCOO]-130.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Iminodiacetic acidOC(=O)CNCC(O)=O2153.7Standard polar33892256
Iminodiacetic acidOC(=O)CNCC(O)=O1188.6Standard non polar33892256
Iminodiacetic acidOC(=O)CNCC(O)=O1395.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Iminodiacetic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CNCC(=O)O1404.7Semi standard non polar33892256
Iminodiacetic acid,1TMS,isomer #2C[Si](C)(C)N(CC(=O)O)CC(=O)O1440.6Semi standard non polar33892256
Iminodiacetic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CNCC(=O)O[Si](C)(C)C1468.1Semi standard non polar33892256
Iminodiacetic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CN(CC(=O)O)[Si](C)(C)C1544.1Semi standard non polar33892256
Iminodiacetic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1576.8Semi standard non polar33892256
Iminodiacetic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1550.3Standard non polar33892256
Iminodiacetic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1665.3Standard polar33892256
Iminodiacetic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNCC(=O)O1675.8Semi standard non polar33892256
Iminodiacetic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CC(=O)O)CC(=O)O1709.9Semi standard non polar33892256
Iminodiacetic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNCC(=O)O[Si](C)(C)C(C)(C)C1922.2Semi standard non polar33892256
Iminodiacetic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CN(CC(=O)O)[Si](C)(C)C(C)(C)C1997.8Semi standard non polar33892256
Iminodiacetic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2212.3Semi standard non polar33892256
Iminodiacetic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2166.6Standard non polar33892256
Iminodiacetic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2081.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Iminodiacetic acid GC-MS (2 TMS)splash10-03dl-1900000000-bc536bd33b5bb4d504f12014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Iminodiacetic acid GC-MS (3 TMS)splash10-001i-5980000000-f8e3bf4eb6a737036f632014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Iminodiacetic acid GC-MS (Non-derivatized)splash10-03dl-1900000000-bc536bd33b5bb4d504f12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Iminodiacetic acid GC-MS (Non-derivatized)splash10-001i-5980000000-f8e3bf4eb6a737036f632017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Iminodiacetic acid GC-EI-TOF (Non-derivatized)splash10-001i-1960000000-42f0b8b3958f9e85b38f2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iminodiacetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9100000000-451fcc1fe69f887e037c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iminodiacetic acid GC-MS (2 TMS) - 70eV, Positivesplash10-03k9-9740000000-ce4b506cbc11cc8c9ca42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iminodiacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iminodiacetic acid 10V, Positive-QTOFsplash10-001r-6900000000-ce1ff0b0bde548998e5a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iminodiacetic acid 20V, Positive-QTOFsplash10-000i-9300000000-7ffe6ab49ebab30d1c882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iminodiacetic acid 40V, Positive-QTOFsplash10-0006-9000000000-8aa1d405b1000e5ce9172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iminodiacetic acid 10V, Negative-QTOFsplash10-001i-1900000000-0520ac09c2ffb0ca305a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iminodiacetic acid 20V, Negative-QTOFsplash10-001i-3900000000-57e171a290e264d2ca9d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iminodiacetic acid 40V, Negative-QTOFsplash10-0buc-9200000000-dec8a7def44b6da0fc202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iminodiacetic acid 10V, Positive-QTOFsplash10-000i-9400000000-57ab56c449e819d943182021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iminodiacetic acid 20V, Positive-QTOFsplash10-000f-9000000000-9b3c69cf26b28b50903a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iminodiacetic acid 40V, Positive-QTOFsplash10-0006-9000000000-7691ad1fbfdd9e5699592021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iminodiacetic acid 10V, Negative-QTOFsplash10-000i-9600000000-3ebb5cf862bee16e9bb32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iminodiacetic acid 20V, Negative-QTOFsplash10-000i-9000000000-e0c6b60e6e3064d4c44c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iminodiacetic acid 40V, Negative-QTOFsplash10-0006-9000000000-e72dda8bd4f92441e1c62021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1251231
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]