ContaminantDB: Edetic Acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2014-10-14 21:16:22 UTC

Update Date

2016-10-28 10:02:22 UTC

Accession Number

CHEM003931

Identification

Common Name

Edetic Acid

Class

Small Molecule

Description

A chelating agent (chelating agents) that sequesters a variety of polyvalent cations. It is used in pharmaceutical manufacturing and as a food additive. [PubChem]

Contaminant Sources

Clean Air Act Chemicals
Cosmetic Chemicals
EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Anticoagulant
Chelating Agent
Drug
Food Additive
Metabolite
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(Ethylenedinitrilo)tetraacetic acid, ion(4-)	ChEBI
2,2',2'',2'''-(ethane-1,2-diyldinitrilo)tetraacetate	ChEBI
Acide edetique	ChEBI
Acide ethylenediaminetetracetique	ChEBI
Acido edetico	ChEBI
Acidum edeticum	ChEBI
EDTA	ChEBI
EDTA, ion(4-)	ChEBI
Ethylenediaminetetraacetate	ChEBI
H4EDta	ChEBI
N,N'-1,2-ethane diylbis-(N-(carboxymethyl)glycine)	ChEBI
{[-(bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetIC ACID	ChEBI
Ethylenediaminetetraacetic acid	Kegg
Versene acid	Kegg
(Ethylenedinitrilo)tetraacetate, ion(4-)	Generator
2,2',2'',2'''-(ethane-1,2-diyldinitrilo)tetraacetic acid	Generator
{[-(bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetate	Generator
Edetate	Generator
CaEDTA	HMDB
Calcium disodium edetate	HMDB
Calcium disodium versenate	HMDB
Edetate calcium	HMDB
Edetate calcium disodium	HMDB
EDT	HMDB
Acid, ethylenedinitrilotetraacetic	HMDB
Calcium tetacine	HMDB
Copper edta	HMDB
EDTA, disodium	HMDB
EDTA, distannous	HMDB
Edathamil	HMDB
Edetates	HMDB
Edetic acid, dipotassium salt	HMDB
Edetic acid, disodium salt, dihydrate	HMDB
Edetic acid, disodium, magnesium salt	HMDB
Edetic acid, magnesium salt	HMDB
Ethylenedinitrilotetraacetic acid	HMDB
N,N'-1,2-ethanediylbis(N-(carboxymethyl)glycine)	HMDB
Potassium edta	HMDB
Chromium edta	HMDB
Coprin	HMDB
Dinitrilotetraacetate, ethylene	HMDB
Disodium ethylene dinitrilotetraacetate	HMDB
Distannous edta	HMDB
EDTA, chromium	HMDB
EDTA, dicobalt	HMDB
EDTA, gallium	HMDB
EDTA, magnesium disodium	HMDB
Edetate disodium calcium	HMDB
Edetic acid, disodium salt	HMDB
Edetic acid, monosodium salt	HMDB
Edetic acid, potassium salt	HMDB
Gallium edta	HMDB
Tetacine, calcium	HMDB
Versene	HMDB
Acid, ethylenediaminetetraacetic	HMDB
Calcitetracemate, disodium	HMDB
Chelaton 3	HMDB
Dinitrilotetraacetate, disodium ethylene	HMDB
Disodium edta	HMDB
EDTA, copper	HMDB
Edetic acid, sodium salt	HMDB
Ethylene dinitrilotetraacetate, disodium	HMDB
Stannous edta	HMDB
Tetracemate	HMDB
Versenate	HMDB
Versenate, calcium disodium	HMDB
Acid, edetic	HMDB
Dicobalt edta	HMDB
Disodium calcitetracemate	HMDB
Disodium versenate, calcium	HMDB
EDTA, potassium	HMDB
EDTA, stannous	HMDB
Edetate, calcium disodium	HMDB
Edetic acid, calcium salt	HMDB
Edetic acid, calcium, sodium salt	HMDB
Edetic acid, chromium salt	HMDB
Edetic acid, disodium, monopotassium salt	HMDB
Edetic acid, monopotassium salt	HMDB
Ethylene dinitrilotetraacetate	HMDB
Magnesium disodium edta	HMDB
Edetic acid	ChEBI

Chemical Formula

C₁₀H₁₆N₂O₈

Average Molecular Mass

292.243 g/mol

Monoisotopic Mass

292.091 g/mol

CAS Registry Number

62-33-9

IUPAC Name

2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetic acid

Traditional Name

edta

SMILES

OC(=O)CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O

InChI Identifier

InChI=1S/C10H16N2O8/c13-7(14)3-11(4-8(15)16)1-2-12(5-9(17)18)6-10(19)20/h1-6H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20)

InChI Key

KCXVZYZYPLLWCC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
Amino acid or derivatives
Tertiary amine
Tertiary aliphatic amine
Amino acid
Carboxylic acid
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Amine
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ethylenediamine derivative (CHEBI:42191 )
polyamino carboxylic acid (CHEBI:42191 )
tetracarboxylic acid (CHEBI:42191 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	237 °C
Boiling Point	Not Available
Solubility	1000000 mg/L at 25 °C

Predicted Properties

Property	Value	Source
Water Solubility	9.26 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-4.9	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	2.35	ChemAxon
pKa (Strongest Basic)	7.73	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	155.68 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	62.35 m³·mol⁻¹	ChemAxon
Polarizability	25.64 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0f6x-2971000000-52370879752b5b63ccc2	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f6x-2971000000-52370879752b5b63ccc2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-3930000000-da498c10e1988a598601	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-00dl-9253520000-45cc304de47f6d8bb25f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0007-0190000000-ff2f56ae902dbe88ddae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1970000000-6acfba9be031774d58fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w2i-4980000000-7fb5e96677fc6ff6c029	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-fdc1ce0a492732d97d45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0290000000-6ea2ca75f62b63f02ce2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-8920000000-d825f98fdc0554f6dc69	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0190000000-c31f2cd2d6c009257aef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-7aeb329bb5d0bb75f7c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ika-4900000000-f34d98ee3d0ba2dd49e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-5ff618f36425e9cee334	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-0290000000-9e41e44730ef5a58a845	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btc-6900000000-20eadce392ac9f0f0acd	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Poorly absorbed from the gastrointestinal tract. Well absorbed following intramuscular injection.

Mechanism of Toxicity

The pharmacologic effects of edetate calcium disodium are due to the formation of chelates with divalent and trivalent metals. A stable chelate will form with any metal that has the ability to displace calcium from the molecule, a feature shared by lead, zinc, cadmium, manganese, iron and mercury. The amounts of manganese and iron metabolized are not significant. Copper is not mobilized and mercury is unavailable for chelation because it is too tightly bound to body ligands or it is stored in inaccessible body compartments. The excretion of calcium by the body is not increased following intravenous administration of edetate calcium disodium, but the excretion of zinc is considerably increased.

Metabolism

Almost none of the compound is metabolized.

Toxicity Values

Inadvertent administration of 5 times the recommended dose, infused intravenously over a 24 hour period, to an asymptomatic 16 month old patient with a blood lead content of 56 mcg/dl did not cause any ill effects. Edetate calcium disodium can aggravate the symptoms of severe lead poisoning, therefore, most toxic effects (cerebral edema, renal tubular necrosis) appear to be associated with lead poisoning. Because of cerebral edema, a therapeutic dose may be lethal to an adult or a pediatric patient with lead encephalopathy. Higher dosage of edetate calcium disodium may produce a more severe zinc deficiency.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the reduction of blood levels and depot stores of lead in lead poisoning (acute and chronic) and lead encephalopathy, in both pediatric populations and adults.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID