Nitrilotriacetic acid

Identification

Generic Name
Nitrilotriacetic acid
DrugBank Accession Number
DB03040
Background

Nitrilotriacetic acid is a derivative of acetic acid, N(CH2COOH)3. It is a complexing (sequestering) agent that forms stable complexes with Zn2+. (From Miall's Dictionary of Chemistry, 5th ed.)

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 191.1388
Monoisotopic: 191.042987025
Chemical Formula
C6H9NO6
Synonyms
  • nitrilo-2,2',2''-triacetic acid
  • Nitrilotriacetate
  • Triglycine
  • Triglycollamic acid
  • α,α',α''-trimethylaminetricarboxylic acid
External IDs
  • CHEL 300

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ULactotransferrinNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Technetium Tc-99m oxidronateNitrilotriacetic acid may decrease effectiveness of Technetium Tc-99m oxidronate as a diagnostic agent.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
Tricarboxylic acids and derivatives / Trialkylamines / Amino acids / Carboxylic acids / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Alpha-amino acid / Amine / Amino acid / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
NTA, tricarboxylic acid (CHEBI:44557)
Affected organisms
Not Available

Chemical Identifiers

UNII
KA90006V9D
CAS number
139-13-9
InChI Key
MGFYIUFZLHCRTH-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-[bis(carboxymethyl)amino]acetic acid
SMILES
OC(=O)CN(CC(O)=O)CC(O)=O

References

General References
Not Available
KEGG Compound
C14695
PubChem Compound
8758
PubChem Substance
46504710
ChemSpider
8428
ChEBI
44557
ChEMBL
CHEMBL1234848
ZINC
ZINC000001849692
PDBe Ligand
NTA
Wikipedia
Nitrilotriacetic_acid
PDB Entries
1gvc / 1nft / 3ufk / 4h0w / 5x5p / 7ffm

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility31.7 mg/mLALOGPS
logP-0.98ALOGPS
logP-4.3Chemaxon
logS-0.78ALOGPS
pKa (Strongest Acidic)1.97Chemaxon
pKa (Strongest Basic)8.63Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area115.14 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity38.24 m3·mol-1Chemaxon
Polarizability16.12 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6349
Blood Brain Barrier+0.5294
Caco-2 permeable-0.5832
P-glycoprotein substrateNon-substrate0.6426
P-glycoprotein inhibitor INon-inhibitor0.9762
P-glycoprotein inhibitor IINon-inhibitor0.9587
Renal organic cation transporterNon-inhibitor0.9015
CYP450 2C9 substrateNon-substrate0.8326
CYP450 2D6 substrateNon-substrate0.8717
CYP450 3A4 substrateNon-substrate0.7577
CYP450 1A2 substrateNon-inhibitor0.8886
CYP450 2C9 inhibitorNon-inhibitor0.9616
CYP450 2D6 inhibitorNon-inhibitor0.891
CYP450 2C19 inhibitorNon-inhibitor0.9402
CYP450 3A4 inhibitorNon-inhibitor0.9562
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.988
Ames testNon AMES toxic0.9258
CarcinogenicityNon-carcinogens0.6724
BiodegradationNot ready biodegradable0.6697
Rat acute toxicity2.2087 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9271
hERG inhibition (predictor II)Non-inhibitor0.9609
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-47e4acf27f01ab04283e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-3866675944ad6d01ede3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-007t-5900000000-73cb38b2d69081a3ce63
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udj-0900000000-aa34e6072a437781b36d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-97e599f277cf0c23c71c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-d9f3da80570ac9d539ad
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-138.4079034
predicted
DarkChem Lite v0.1.0
[M-H]-131.752
predicted
DeepCCS 1.0 (2019)
[M+H]+138.2160034
predicted
DarkChem Lite v0.1.0
[M+H]+135.5738
predicted
DeepCCS 1.0 (2019)
[M+Na]+138.4901034
predicted
DarkChem Lite v0.1.0
[M+Na]+144.963
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Transferrins are iron binding transport proteins which can bind two Fe(3+) ions in association with the binding of an anion, usually bicarbonate.Lactotransferrin is a major iron-binding and multifu...
Gene Name
LTF
Uniprot ID
P02788
Uniprot Name
Lactotransferrin
Molecular Weight
78181.225 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52