T3DB: Edetic Acid

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

Targets (3)

Record Information

Version

2.0

Creation Date

2014-10-14 21:16:22 UTC

Update Date

2014-12-24 20:27:01 UTC

Accession Number

T3D4977

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]

Compound Type

Anticoagulant
Chelating Agent
Drug
Food Additive
Metabolite
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
(ethane-1,2-diyldinitrilo)tetraacetic acid
(Ethylenedinitrilo)tetraacetic acid
2,2',2'',2'''-(1,2-Ethanediyldinitrilo)tetraacetic acid
2,2',2'',2'''-(ethane-1,2-diyldinitrilo)tetraacetic acid
EDTA
Ethylenediamine tetraacetic acid
Ethylenediaminetetraacetic acid
N,N'-1,2-Ethanediylbis[N-(carboxymethyl)glycine]

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

InChIKey=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
LogP	-2.6

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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

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

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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

EDT

ACToR ID

Not Available

Wikipedia Link

EDTA

References

Synthesis Reference

Bersworth, F.C.; U.S. Patent 2,407,645; September 17,1946; assigned to The Martin Dennis Co.

MSDS

T3D4977.pdf

General References

Not Available

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

1. Lead

References

Onnby L, Giorgi C, Plieva FM, Mattiasson B: Removal of heavy metals from water effluents using supermacroporous metal chelating cryogels. Biotechnol Prog. 2010 Sep-Oct;26(5):1295-302. doi: 10.1002/btpr.422. [20945486 ]
Chakraborty N, Banerjee A, Pal R: Accumulation of lead by free and immobilized cyanobacteria with special reference to accumulation factor and recovery. Bioresour Technol. 2011 Mar;102(5):4191-5. doi: 10.1016/j.biortech.2010.12.028. Epub 2010 Dec 13. [21195608 ]
Tian SK, Lu LL, Yang XE, Huang HG, Brown P, Labavitch J, Liao HB, He ZL: The impact of EDTA on lead distribution and speciation in the accumulator Sedum alfredii by synchrotron X-ray investigation. Environ Pollut. 2011 Mar;159(3):782-8. doi: 10.1016/j.envpol.2010.11.020. Epub 2010 Dec 18. [21168940 ]

2. Iron

References

Hasegawa H, Rahman IM, Kinoshita S, Maki T, Furusho Y: Separation of dissolved iron from the aqueous system with excess ligand. Chemosphere. 2011 Feb;82(8):1161-7. doi: 10.1016/j.chemosphere.2010.12.048. Epub 2011 Jan 3. [21208637 ]

3. Manganese cation

References

Broncel M, Wagner SC, Paul K, Hackenberger CP, Koksch B: Towards understanding secondary structure transitions: phosphorylation and metal coordination in model peptides. Org Biomol Chem. 2010 Jun 7;8(11):2575-9. doi: 10.1039/c001458c. Epub 2010 Mar 29. [20485793 ]

Edetic Acid (T3D4977)

Structure for T3D4977: Edetic Acid

Targets

References

References

References