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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-03-17 13:28:50 UTC

Update Date

2023-02-21 17:17:36 UTC

HMDB ID

HMDB0011753

Secondary Accession Numbers

HMDB11753

Metabolite Identification

Common Name

Iminodiacetic acid

Description

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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,2'-Azanediyldiacetic acid	ChEBI
2-[(Carboxymethyl)amino]acetic acid	ChEBI
Aminodiacetic acid	ChEBI
Bis(carboxymethyl)amine	ChEBI
Diglycine	ChEBI
Diglycocoll	ChEBI
IDA	ChEBI
Iminobis(acetic acid)	ChEBI
Iminodiethanoic acid	ChEBI
N-(Carboxymethyl)glycine	ChEBI
2,2'-Azanediyldiacetate	Generator
2-[(Carboxymethyl)amino]acetate	Generator
Aminodiacetate	Generator
Iminobis(acetate)	Generator
Iminodiethanoate	Generator
Iminodiacetate	Generator
Imidodiacetic acid	MeSH
Iminodiacetic acid, disodium salt	MeSH
Iminodiacetic acid, calcium salt (1:1)	MeSH
Iminodiacetic acid, sodium salt	MeSH
2,2'-Iminodiacetic acid	ChEBI
2,2'-Iminodiacetate	Generator
N-(Carboxymethyl)- glycine	HMDB
Iminodiacetic acid	Generator

Chemical Formula

C₄H₇NO₄

Average Molecular Weight

133.1027

Monoisotopic Molecular Weight

133.037507717

IUPAC Name

2-[(carboxymethyl)amino]acetic acid

Traditional Name

iminodiacetic acid

CAS Registry Number

142-73-4

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 Key

NBZBKCUXIYYUSX-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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic acyclic compounds

External Descriptors

glycine derivative (CHEBI:24786 )
amino dicarboxylic acid (CHEBI:24786 )
non-proteinogenic alpha-amino acid (CHEBI:24786 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0011753)

Excreta

Biofluid or Excreta

Urine (PMID: 21543078)

Source

Exogenous

Exogenous (HMDB: HMDB0011753)

Process

Not Available

Role

Industrial application

Drug (HMDB: HMDB0011753)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	247.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	370.56 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	475800 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.840 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	36.9 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-4.1	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	2.12	ChemAxon
pKa (Strongest Basic)	8.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	26.86 m³·mol⁻¹	ChemAxon
Polarizability	11.63 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.447	31661259
DarkChem	[M-H]-	121.413	31661259
DeepCCS	[M+H]+	126.469	30932474
DeepCCS	[M-H]-	123.661	30932474
DeepCCS	[M-2H]-	160.036	30932474
DeepCCS	[M+Na]+	135.031	30932474
AllCCS	[M+H]+	129.8	32859911
AllCCS	[M+H-H2O]+	125.7	32859911
AllCCS	[M+NH4]+	133.5	32859911
AllCCS	[M+Na]+	134.6	32859911
AllCCS	[M-H]-	124.8	32859911
AllCCS	[M+Na-2H]-	127.5	32859911
AllCCS	[M+HCOO]-	130.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Iminodiacetic acid	OC(=O)CNCC(O)=O	2153.7	Standard polar	33892256
Iminodiacetic acid	OC(=O)CNCC(O)=O	1188.6	Standard non polar	33892256
Iminodiacetic acid	OC(=O)CNCC(O)=O	1395.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Iminodiacetic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CNCC(=O)O	1404.7	Semi standard non polar	33892256
Iminodiacetic acid,1TMS,isomer #2	C[Si](C)(C)N(CC(=O)O)CC(=O)O	1440.6	Semi standard non polar	33892256
Iminodiacetic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CNCC(=O)O[Si](C)(C)C	1468.1	Semi standard non polar	33892256
Iminodiacetic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CN(CC(=O)O)[Si](C)(C)C	1544.1	Semi standard non polar	33892256
Iminodiacetic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1576.8	Semi standard non polar	33892256
Iminodiacetic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1550.3	Standard non polar	33892256
Iminodiacetic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1665.3	Standard polar	33892256
Iminodiacetic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNCC(=O)O	1675.8	Semi standard non polar	33892256
Iminodiacetic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(=O)O)CC(=O)O	1709.9	Semi standard non polar	33892256
Iminodiacetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNCC(=O)O[Si](C)(C)C(C)(C)C	1922.2	Semi standard non polar	33892256
Iminodiacetic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CN(CC(=O)O)[Si](C)(C)C(C)(C)C	1997.8	Semi standard non polar	33892256
Iminodiacetic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2212.3	Semi standard non polar	33892256
Iminodiacetic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2166.6	Standard non polar	33892256
Iminodiacetic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2081.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Iminodiacetic acid GC-MS (2 TMS)	splash10-03dl-1900000000-bc536bd33b5bb4d504f1	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Iminodiacetic acid GC-MS (3 TMS)	splash10-001i-5980000000-f8e3bf4eb6a737036f63	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Iminodiacetic acid GC-MS (Non-derivatized)	splash10-03dl-1900000000-bc536bd33b5bb4d504f1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Iminodiacetic acid GC-MS (Non-derivatized)	splash10-001i-5980000000-f8e3bf4eb6a737036f63	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Iminodiacetic acid GC-EI-TOF (Non-derivatized)	splash10-001i-1960000000-42f0b8b3958f9e85b38f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iminodiacetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9100000000-451fcc1fe69f887e037c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iminodiacetic acid GC-MS (2 TMS) - 70eV, Positive	splash10-03k9-9740000000-ce4b506cbc11cc8c9ca4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iminodiacetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminodiacetic acid 10V, Positive-QTOF	splash10-001r-6900000000-ce1ff0b0bde548998e5a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminodiacetic acid 20V, Positive-QTOF	splash10-000i-9300000000-7ffe6ab49ebab30d1c88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminodiacetic acid 40V, Positive-QTOF	splash10-0006-9000000000-8aa1d405b1000e5ce917	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminodiacetic acid 10V, Negative-QTOF	splash10-001i-1900000000-0520ac09c2ffb0ca305a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminodiacetic acid 20V, Negative-QTOF	splash10-001i-3900000000-57e171a290e264d2ca9d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminodiacetic acid 40V, Negative-QTOF	splash10-0buc-9200000000-dec8a7def44b6da0fc20	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminodiacetic acid 10V, Positive-QTOF	splash10-000i-9400000000-57ab56c449e819d94318	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminodiacetic acid 20V, Positive-QTOF	splash10-000f-9000000000-9b3c69cf26b28b50903a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminodiacetic acid 40V, Positive-QTOF	splash10-0006-9000000000-7691ad1fbfdd9e569959	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminodiacetic acid 10V, Negative-QTOF	splash10-000i-9600000000-3ebb5cf862bee16e9bb3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminodiacetic acid 20V, Negative-QTOF	splash10-000i-9000000000-e0c6b60e6e3064d4c44c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminodiacetic acid 40V, Negative-QTOF	splash10-0006-9000000000-e72dda8bd4f92441e1c6	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected but not Quantified	Not Quantified	Not Available	Not Available	Normal	21543078	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Iminodiacetic_acid

METLIN ID

Not Available

PubChem Compound

8897

PDB ID

Not Available

ChEBI ID

24786

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1251231

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]

Showing metabocard for Iminodiacetic acid (HMDB0011753)

MOL for HMDB0011753 (Iminodiacetic acid)

3D MOL for HMDB0011753 (Iminodiacetic acid)

3D SDF for HMDB0011753 (Iminodiacetic acid)

3D-SDF for HMDB0011753 (Iminodiacetic acid)

PDB for HMDB0011753 (Iminodiacetic acid)

3D PDB for HMDB0011753 (Iminodiacetic acid)

SMILES for HMDB0011753 (Iminodiacetic acid)

INCHI for HMDB0011753 (Iminodiacetic acid)

Structure for HMDB0011753 (Iminodiacetic acid)

3D Structure for HMDB0011753 (Iminodiacetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra