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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:25:09 UTC

Update Date

2021-09-26 23:10:38 UTC

HMDB ID

HMDB0255635

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nitrilotriacetic acid

Description

Nitrilotriacetic acid, also known as nitrilotriacetate or H3NTA, 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). The his-tag binds the metal of metal chelator complexes. Despite widespread use in cleaning products, the concentration in the water supply is too low to have a sizeable impact on human health or environmental quality. Nitrilotriacetic acid is a very strong basic compound (based on its pKa). Nitrilotriacetic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. In one application, NTA as a chelating agent removes Cr, Cu, and As from wood that had been treated with chromated copper arsenate. NTA is a tripodal tetradentate trianionic ligand. This compound has been identified in human blood as reported by (PMID: 31557052 ). Nitrilotriacetic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Nitrilotriacetic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       2.667  -8.827   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -7.287   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -6.517   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -6.517   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.334  -4.977   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.000  -4.207   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -1.897   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.334  -1.897   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -4.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -2.667   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.041  -1.261   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001  -1.897   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha,Alpha',alpha''-trimethylaminetricarboxylic acid	ChEBI
Complexon I	ChEBI
H3Nta	ChEBI
Komplexon I	ChEBI
N(CH2-COOH)3	ChEBI
Nitrilo-2,2',2''-triacetic acid	ChEBI
Nitrilotriacetate	ChEBI
Nitrilotriessigsaeure	ChEBI
NTA	ChEBI
Tri(carboxymethyl)amine	ChEBI
Triglycine	ChEBI
Triglycollamic acid	ChEBI
Trilon a	ChEBI
a,Alpha',alpha''-trimethylaminetricarboxylate	Generator
a,Alpha',alpha''-trimethylaminetricarboxylic acid	Generator
alpha,Alpha',alpha''-trimethylaminetricarboxylate	Generator
Α,alpha',alpha''-trimethylaminetricarboxylate	Generator
Α,alpha',alpha''-trimethylaminetricarboxylic acid	Generator
Nitrilo-2,2',2''-triacetate	Generator
Triglycollamate	Generator
Dysprosium nitrilotriacetate	MeSH
Trisodium nitrilotriacetate	MeSH
Nitrilotriacetate, dysprosium	MeSH
Nitrilotriacetate, aluminum	MeSH
Aluminum nitrilotriacetate	MeSH
Nitrilotriacetate, trisodium	MeSH
Acid, nitrilotriacetic	MeSH

Chemical Formula

C₆H₉NO₆

Average Molecular Weight

191.1388

Monoisotopic Molecular Weight

191.042987025

IUPAC Name

2-[bis(carboxymethyl)amino]acetic acid

Traditional Name

nitrilotriacetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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)

InChI Key

MGFYIUFZLHCRTH-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

NTA (CHEBI:44557 )
tricarboxylic acid (CHEBI:44557 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0255635)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.98	ALOGPS
logP	-2.1	ChemAxon
logS	-0.78	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	5.58	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	115.14 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	38.24 m³·mol⁻¹	ChemAxon
Polarizability	16.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	135.574	30932474
DeepCCS	[M-H]-	131.752	30932474
DeepCCS	[M-2H]-	169.424	30932474
DeepCCS	[M+Na]+	144.963	30932474
AllCCS	[M+H]+	140.5	32859911
AllCCS	[M+H-H2O]+	136.9	32859911
AllCCS	[M+NH4]+	143.9	32859911
AllCCS	[M+Na]+	144.8	32859911
AllCCS	[M-H]-	134.6	32859911
AllCCS	[M+Na-2H]-	135.9	32859911
AllCCS	[M+HCOO]-	137.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nitrilotriacetic acid	OC(=O)CN(CC(O)=O)CC(O)=O	2621.4	Standard polar	33892256
Nitrilotriacetic acid	OC(=O)CN(CC(O)=O)CC(O)=O	1418.8	Standard non polar	33892256
Nitrilotriacetic acid	OC(=O)CN(CC(O)=O)CC(O)=O	1790.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nitrilotriacetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-4900000000-d49516fc27821cc46bb0	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitrilotriacetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitrilotriacetic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitrilotriacetic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitrilotriacetic acid GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitrilotriacetic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitrilotriacetic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitrilotriacetic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitrilotriacetic acid 10V, Positive-QTOF	splash10-0006-0900000000-0776b51aff948512105b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitrilotriacetic acid 20V, Positive-QTOF	splash10-0006-0900000000-e0267756ed6f22cb98e8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitrilotriacetic acid 40V, Positive-QTOF	splash10-000i-9700000000-cca6b7d9ebca4e2d090b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitrilotriacetic acid 10V, Negative-QTOF	splash10-0006-0900000000-363abbab9912302e3f8f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitrilotriacetic acid 20V, Negative-QTOF	splash10-0006-0900000000-3a65d9e27f0a7cb61efb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitrilotriacetic acid 40V, Negative-QTOF	splash10-052g-5900000000-2609b4ede188bad3629c	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03040

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14695

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nitrilotriacetic acid

METLIN ID

Not Available

PubChem Compound

8758

PDB ID

Not Available

ChEBI ID

44557

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Nitrilotriacetic acid (HMDB0255635)

MOL for HMDB0255635 (Nitrilotriacetic acid)

3D MOL for HMDB0255635 (Nitrilotriacetic acid)

3D SDF for HMDB0255635 (Nitrilotriacetic acid)

3D-SDF for HMDB0255635 (Nitrilotriacetic acid)

PDB for HMDB0255635 (Nitrilotriacetic acid)

3D PDB for HMDB0255635 (Nitrilotriacetic acid)

SMILES for HMDB0255635 (Nitrilotriacetic acid)

INCHI for HMDB0255635 (Nitrilotriacetic acid)

Structure for HMDB0255635 (Nitrilotriacetic acid)

3D Structure for HMDB0255635 (Nitrilotriacetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra