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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:40:59 UTC
HMDB IDHMDB0015109
Secondary Accession Numbers
  • HMDB15109
Metabolite Identification
Common NameEdetic Acid
DescriptionEdetic Acid is only found in individuals that have used or taken this drug. It is a chelating agent (chelating agents) that sequesters a variety of polyvalent cations. It is used in pharmaceutical manufacturing and as a food additive. [PubChem]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.
Structure
Data?1582753259
Synonyms
ValueSource
(Ethylenedinitrilo)tetraacetic acid, ion(4-)ChEBI
2,2',2'',2'''-(ethane-1,2-diyldinitrilo)tetraacetateChEBI
Acide edetiqueChEBI
Acide ethylenediaminetetracetiqueChEBI
Acido edeticoChEBI
Acidum edeticumChEBI
EDTAChEBI
EDTA, ion(4-)ChEBI
EthylenediaminetetraacetateChEBI
H4EDtaChEBI
N,N'-1,2-ethane diylbis-(N-(carboxymethyl)glycine)ChEBI
{[-(bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetIC ACIDChEBI
Ethylenediaminetetraacetic acidKegg
Versene acidKegg
(Ethylenedinitrilo)tetraacetate, ion(4-)Generator
2,2',2'',2'''-(ethane-1,2-diyldinitrilo)tetraacetic acidGenerator
{[-(bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetateGenerator
EdetateGenerator
CaEDTAHMDB
Calcium disodium edetateHMDB
Calcium disodium versenateHMDB
Edetate calciumHMDB
Edetate calcium disodiumHMDB
EDTHMDB
Acid, ethylenedinitrilotetraaceticHMDB
Calcium tetacineHMDB
Copper edtaHMDB
EDTA, disodiumHMDB
EDTA, distannousHMDB
EdathamilHMDB
EdetatesHMDB
Edetic acid, dipotassium saltHMDB
Edetic acid, disodium salt, dihydrateHMDB
Edetic acid, disodium, magnesium saltHMDB
Edetic acid, magnesium saltHMDB
Ethylenedinitrilotetraacetic acidHMDB
N,N'-1,2-ethanediylbis(N-(carboxymethyl)glycine)HMDB
Potassium edtaHMDB
Chromium edtaHMDB
CoprinHMDB
Dinitrilotetraacetate, ethyleneHMDB
Disodium ethylene dinitrilotetraacetateHMDB
Distannous edtaHMDB
EDTA, chromiumHMDB
EDTA, dicobaltHMDB
EDTA, galliumHMDB
EDTA, magnesium disodiumHMDB
Edetate disodium calciumHMDB
Edetic acid, disodium saltHMDB
Edetic acid, monosodium saltHMDB
Edetic acid, potassium saltHMDB
Gallium edtaHMDB
Tetacine, calciumHMDB
VerseneHMDB
Acid, ethylenediaminetetraaceticHMDB
Calcitetracemate, disodiumHMDB
Chelaton 3HMDB
Dinitrilotetraacetate, disodium ethyleneHMDB
Disodium edtaHMDB
EDTA, copperHMDB
Edetic acid, sodium saltHMDB
Ethylene dinitrilotetraacetate, disodiumHMDB
Stannous edtaHMDB
TetracemateHMDB
VersenateHMDB
Versenate, calcium disodiumHMDB
Acid, edeticHMDB
Dicobalt edtaHMDB
Disodium calcitetracemateHMDB
Disodium versenate, calciumHMDB
EDTA, potassiumHMDB
EDTA, stannousHMDB
Edetate, calcium disodiumHMDB
Edetic acid, calcium saltHMDB
Edetic acid, calcium, sodium saltHMDB
Edetic acid, chromium saltHMDB
Edetic acid, disodium, monopotassium saltHMDB
Edetic acid, monopotassium saltHMDB
Ethylene dinitrilotetraacetateHMDB
Magnesium disodium edtaHMDB
Edetic acidChEBI
Chemical FormulaC10H16N2O8
Average Molecular Weight292.2426
Monoisotopic Molecular Weight292.090665498
IUPAC Name2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetic acid
Traditional Nameedta
CAS Registry Number62-33-9
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 KeyKCXVZYZYPLLWCC-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTetracarboxylic acids and derivatives
Direct ParentTetracarboxylic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Route of exposure:

Biological location:

Role

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.26 g/LNot Available
LogP-2.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility9.26 g/LALOGPS
logP-1.2ALOGPS
logP-4.9ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.35ChemAxon
pKa (Strongest Basic)7.73ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area155.68 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity62.35 m³·mol⁻¹ChemAxon
Polarizability25.64 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f6x-2971000000-52370879752b5b63ccc2Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f6x-2971000000-52370879752b5b63ccc2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-3930000000-da498c10e1988a598601Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00dl-9253520000-45cc304de47f6d8bb25fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-0190000000-ff2f56ae902dbe88ddaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1970000000-6acfba9be031774d58fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w2i-4980000000-7fb5e96677fc6ff6c029Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-fdc1ce0a492732d97d45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0290000000-6ea2ca75f62b63f02ce2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-8920000000-d825f98fdc0554f6dc69Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00974 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00974 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00974
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5826
KEGG Compound IDC00284
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEdetate
METLIN IDNot Available
PubChem Compound6049
PDB IDEDT
ChEBI ID42191
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in arylesterase activity
Specific function:
Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:
PON3
Uniprot ID:
Q15166
Molecular weight:
39607.185
References
  1. Pla A, Rodrigo L, Hernandez AF, Gil F, Lopez O: Effect of metal ions and calcium on purified PON1 and PON3 from rat liver. Chem Biol Interact. 2007 Apr 5;167(1):63-70. Epub 2007 Jan 16. [PubMed:17292339 ]
General function:
Involved in deaminase activity
Specific function:
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion.
Gene Name:
ADA
Uniprot ID:
P00813
Molecular weight:
40764.13
References
  1. Abu-Shady MR, Elshafei AM, el-Beih FM, Mohamed LA: Properties of adenosine deaminase in extracts of Asperigillus terricola. Acta Microbiol Pol. 1994;43(3-4):305-11. [PubMed:7740980 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Bournique B, Petry M, Gousset G: Usefulness of statistic experimental designs in enzymology: example with recombinant hCYP3A4 and 1A2. Anal Biochem. 1999 Dec 1;276(1):18-26. [PubMed:10585740 ]
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
References
  1. Moslemi S, Vibet A, Papadopoulos V, Camoin L, Silberzahn P, Gaillard JL: Purification and characterization of equine testicular cytochrome P-450 aromatase: comparison with the human enzyme. Comp Biochem Physiol B Biochem Mol Biol. 1997 Sep;118(1):217-27. [PubMed:9418012 ]
  2. Bellino FL, Holben L: Placental estrogen synthetase (aromatase): evidence for phosphatase-dependent inactivation. Biochem Biophys Res Commun. 1989 Jul 14;162(1):498-504. [PubMed:2546553 ]
  3. Zhang F, Zhou D, Kao YC, Ye J, Chen S: Expression and purification of a recombinant form of human aromatase from Escherichia coli. Biochem Pharmacol. 2002 Nov 1;64(9):1317-24. [PubMed:12392814 ]
  4. Milczarek R, Sokolowska E, Hallmann A, Kaletha K, Klimek J: NADPH- and iron-dependent lipid peroxidation inhibit aromatase activity in human placental microsomes. J Steroid Biochem Mol Biol. 2008 Jun;110(3-5):230-5. doi: 10.1016/j.jsbmb.2007.11.004. Epub 2008 Apr 20. [PubMed:18499441 ]