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Details

Stereochemistry ACHIRAL
Molecular Formula C6H9NO6
Molecular Weight 191.1388
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Nitrilotriacetic acid

SMILES

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

InChI

InChIKey=MGFYIUFZLHCRTH-UHFFFAOYSA-N
InChI=1S/C6H9NO6/c8-4(9)1-7(2-5(10)11)3-6(12)13/h1-3H2,(H,8,9)(H,10,11)(H,12,13)

HIDE SMILES / InChI
Molecular Formula C6H9NO6
Molecular Weight 191.1388
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

2012
608
PubMed

PubMed

TitleDatePubMed
Synergistic anion and metal binding to the ferric ion-binding protein from Neisseria gonorrhoeae.
2003-01-24
Comparative mutagenicities of bleomycin and ferric-nitrilotriacetate in lacZ mice.
2002-12-10
Simultaneous determination of 3-nitrotyrosine and tyrosine in plasma proteins of rats and assessment of artifactual tyrosine nitration.
2002-11-05
Protective effect of metallothionein-III on DNA damage in response to reactive oxygen species.
2002-10-10
Evaluation of carcinogenic responses in the Eker rat following short-term exposure to selected nephrotoxins and carcinogens.
2002-10-10
Assessment of the ability of the antioxidant cocktail-derived from fermentation of plants with effective microorganisms (EM-X) to modulate oxidative damage in the kidney and liver of rats in vivo: studies upon the profile of poly- and mono-unsaturated fatty acids.
2002-10-05
Adsorption behavior of zinc and cadmium ion on granular activated carbon in singular and binary systems and the influence of nitrilotricetic acid as a complexing agent.
2002-10
pH-Dependent fate and transport of NTA-complexed cobalt through undisturbed cores of fractured shale saprolite.
2002-10
Dissimilatory reduction of Cr(VI), Fe(III), and U(VI) by Cellulomonas isolates.
2002-10
On-column complexation and simultaneous separation of vanadium(IV) and vanadium(V) by capillary electrophoresis with direct UV detection.
2002-10
Correlation between induction of DNA fragmentation in urinary bladder cells from rats and humans and tissue-specific carcinogenic activity.
2002-09-30
Cloning, characterization, and functional studies of a 47-kDa platelet receptor for type III collagen.
2002-09-20
On-column tris(2-carboxyethyl)phosphine reduction and IC5-maleimide labeling during purification of a RpoC fragment on a nickel-nitrilotriacetic acid Column.
2002-08-15
Interferon-alpha enhances biological defense activities against oxidative stress in cultured rat hepatocytes and hepatic stellate cells.
2002-08
Specific binding of integrin alphaIIbbeta3 to RGD peptide immobilized on a nitrilotriacetic acid chip: a surface plasmon resonance study.
2002-08
Effects of phlebotomy on the growth of ferric nitrilotriacetate-induced renal cell carcinoma.
2002-08
Contribution of glutathione and metallothioneins to protection against copper toxicity and redox cycling: quantitative analysis using MT+/+ and MT-/- mouse lung fibroblast cells.
2002-08
Non-transferrin-bound iron in untreated and ribavirin-treated chronic hepatitis C patients.
2002-08
Bioavailability of waterborne strontium to the common carp, Cyprinus carpio, in complexing environments.
2002-08
Development and characterization of Ni-NTA-bearing microspheres.
2002-07-01
Cytotoxic targeting of F9 teratocarcinoma tumours with anti-ED-B fibronectin scFv antibody modified liposomes.
2002-07-01
Purification, reconstitution, and characterization of Na(+)/serine symporter, SstT, of Escherichia coli.
2002-07
Alleviation of the two-cell block of ICR mouse embryos by polyaminocarboxylate metal chelators.
2002-07
Biochemistry and pharmacology of epitope-tagged alpha(1)-adrenergic receptor subtypes.
2002-07
The synergistic anion-binding sites of human transferrin: chemical and physiological effects of site-directed mutagenesis.
2002-06-11
Unusual features for zirconium(IV) binding to human serum transferrin.
2002-06
A novel subtilisin-like serine protease from Thermoanaerobacter yonseiensis KB-1: its cloning, expression, and biochemical properties.
2002-06
The role of metals in site-specific DNA damage with reference to carcinogenesis.
2002-05-01
Protective effect of colored rice over white rice on Fenton reaction-based renal lipid peroxidation in rats.
2002-05
The mechanism of iron uptake by transferrins: the X-ray structures of the 18 kDa NII domain fragment of duck ovotransferrin and its nitrilotriacetate complex.
2002-05
Hydrometallurgical recovery of zinc and lead from electric arc furnace dust using mononitrilotriacetate anion and hexahydrated ferric chloride.
2002-04-26
Comparison of histidine-tag capture chemistries for purification following chemical extraction.
2002-04-12
Carbonic anhydrase inhibitors. A general approach for the preparation of water-soluble sulfonamides incorporating polyamino-polycarboxylate tails and of their metal complexes possessing long-lasting, topical intraocular pressure-lowering properties.
2002-03-28
Relations between clusters of oxidatively damaged nucleotides and active or open nucleosomes in the rat Nth 1 gene.
2002-03-07
Gas chromatographic and mass spectrometric analysis of nitrilotriacetic acid in environmental aqueous samples.
2002-03-07
Nontransferrin-bound iron in the plasma of haemodialysis patients after intravenous iron saccharate infusion.
2002-03
Expression of ayu (Plecoglossus altivelis) Pit-1 in Escherichia coli: its purification and immunohistochemical detection using monoclonal antibody.
2002-03
Overproduction in yeast and rapid and efficient purification of the rabbit SERCA1a Ca(2+)-ATPase.
2002-02-18
Simple cryoprotection and cell dissociation techniques for application of the comet assay to fresh and frozen rat tissues.
2002-02
Specific allelic loss of p16 (INK4A) tumor suppressor gene after weeks of iron-mediated oxidative damage during rat renal carcinogenesis.
2002-02
Oxidative damage and cancer.
2002-02
Bleomycin-detectable iron assay for non-transferrin-bound iron in hematologic malignancies.
2002-02
Potential contact sites between the protein and RNA subunit in the Bacillus subtilis RNase P holoenzyme.
2002-01-25
Iminodiacetate and nitrilotriacetate degradation by Kluyveromyces marxianus IMB3.
2002-01-18
Stimulation and proliferation of primary rat hepatic stellate cells by cytochrome P450 2E1-derived reactive oxygen species.
2002-01
Aqua(nitrilotriacetato)(1,10-phenanthroline)iron(III) monohydrate: a seven-coordinate iron(III) complex.
2002-01
Iron and carcinogenesis: from Fenton reaction to target genes.
2002
Examination of cadmium(II) complexation by the Suwannee River fulvic acid using 113Cd NMR relaxation measurements.
2001-12-15
Assessment of chronic toxicity and carcinogenicity in an accelerated cancer bioassay in rats of moxifloxacin, a quinolone antibiotic.
2001-10
Influence of the glass packing on the contamination of pharmaceutical products by aluminium. Part II: amino acids for parenteral nutrition.
2001
Patents

Patents

05861531
6
08012277
6
JP2007238798A
6
JP2009523595A
6
JP2009523596A
6
JP2009523607A
6
JP4791730B2
6
JP5354591B2
6
JPH01287190A
6
JPH05262710A
6
JPH07109212A
6
JPH10272145A
6
JPS55104359A
6
JPS57109885A
6
JPS61207450A
6
JPS62265255A
6
JPS63159463A
6
JPS63313585A
6
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:38:47 GMT 2025
Edited
by admin
on Mon Mar 31 20:38:47 GMT 2025
Record UNII
KA90006V9D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Nitrilotriacetic acid
HSDB   MI   USP-RS  
Systematic Name English
NSC-2121
Preferred Name English
NITRILOTRIACETIC ACID AND ITS SALTS [IARC]
Common Name English
NITRILOTRIACETIC ACID [HSDB]
Common Name English
NITRILO-N,N,N-TRIACETIC ACID
Systematic Name English
NTA
Common Name English
SODIUM CALCIUM EDETATE IMPURITY A [EP IMPURITY]
Common Name English
A,A',A''-TRIMETHYLAMINETRICARBOXYLIC ACID
Common Name English
NITRILO-2,2',2''-TRIACETIC ACID
Systematic Name English
2,2',2''-NITRILOTRIACETIC ACID
Systematic Name English
NITRILOTRIACETIC ACID [USP-RS]
Common Name English
NITRILOTRIACETIC ACID [MI]
Common Name English
GLYCINE, N,N-BIS(CARBOXYMETHYL)-
Systematic Name English
TRIGLYCOLLAMIC ACID
Common Name English
DISODIUM EDETATE IMPURITY A [EP IMPURITY]
Common Name English
N,N-BIS(CARBOXYMETHYL)GLYCINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C45176
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID6020939
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
DRUG BANK
DB03040
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-355-7
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
CHEBI
44557
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
MERCK INDEX
m7935
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C44408
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
WIKIPEDIA
NITRILOTRIACETIC ACID
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
HSDB
2853
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
FDA UNII
KA90006V9D
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
CAS
139-13-9
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
DAILYMED
KA90006V9D
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
NSC
2121
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
RS_ITEM_NUM
1463950
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
MESH
D009571
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
SMS_ID
300000053476
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
PUBCHEM
8758
Created by admin on Mon Mar 31 20:38:47 GMT 2025 , Edited by admin on Mon Mar 31 20:38:47 GMT 2025
PRIMARY
Related Record Type Details
Structure of DISODIUM NITRILOTRIACETATE MONOHYDRATE
SALT/SOLVATE -> PARENT
Structure of FERRIC NITRILOTRIACETATE
SALT/SOLVATE -> PARENT
Structure of TRIPOTASSIUM NITRILOTRIACETATE
SALT/SOLVATE -> PARENT
Structure of DISODIUM NITRILOACETATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of EDETATE DISODIUM
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of EDETATE CALCIUM DISODIUM ANHYDROUS
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of Nitrilotriacetic acid
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