ChemFOnt: Showing chemical card for Iminodiacetic acid (CFc000007319)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:53:35 UTC

Chemfont ID

CFc000007319

Molecule Identification

Common Name

Iminodiacetic acid

Definition

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 SDF PDB SMILES InChI

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 )

Functional 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

Predicted 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