NP-MRD: Showing NP-Card for Trisodium nitrilotriacetate (NP0338517)

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Record Information

Version

2.0

Created at

2024-09-11 15:51:13 UTC

Updated at

2024-09-11 15:51:13 UTC

NP-MRD ID

NP0338517

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Trisodium nitrilotriacetate

Description

Trisodium nitrilotriacetate was first documented in 1985 (PMID: 3932279).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221182D          

 16 12  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 Na  0  3  0  0  0  0  0  0  0  0  0  0
    1.0018    0.0000    0.0000 Na  0  3  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3439    0.0000 Na  0  3  0  0  0  0  0  0  0  0  0  0
    3.5504   -1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.5504   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -4.1250    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.3510   -3.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4083   -4.1250    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  CHG  6   1   1   2   1   3   1   4  -1  11  -1  16  -1
M  END
> <DATABASE_ID>
NP0338517

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NO6.3Na/c8-4(9)1-7(2-5(10)11)3-6(12)13;;;/h1-3H2,(H,8,9)(H,10,11)(H,12,13);;;/q;3*+1/p-3

> <INCHI_KEY>
DZCAZXAJPZCSCU-UHFFFAOYSA-K

> <FORMULA>
C6H6NNa3O6

> <MOLECULAR_WEIGHT>
257.0842

> <EXACT_MASS>
256.988820954

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
14.975671042985685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
trisodium 2-[bis(carboxylatomethyl)amino]acetate

> <ALOGPS_LOGP>
-0.17

> <JCHEM_LOGP>
-2.0884216896573196

> <ALOGPS_LOGS>
-0.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.6816437412181773

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7801441046489845

> <JCHEM_PKA_STRONGEST_BASIC>
5.580483974493386

> <JCHEM_POLAR_SURFACE_AREA>
123.63

> <JCHEM_REFRACTIVITY>
70.7532

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trisodium nitrilotriacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 Na   UNK     0       0.000   0.000   0.000  0.00  0.00          Na+1
HETATM    2 Na   UNK     0       1.870   0.000   0.000  0.00  0.00          Na+1
HETATM    3 Na   UNK     0       0.000  -6.242   0.000  0.00  0.00          Na+1
HETATM    4  O   UNK     0       6.627  -3.080   0.000  0.00  0.00           O-1
HETATM    5  C   UNK     0       6.627  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.294  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.961  -5.390   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       7.961  -6.930   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.627  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.294  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.960  -7.700   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0       4.389  -5.684   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.295  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.628  -6.930   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.628  -5.390   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      11.962  -7.700   0.000  0.00  0.00           O-1
CONECT    4    5                                                            
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   24    0
END

View in JSmol

Synonyms

Value	Source
N,N-Bis(carboxymethyl)glycine, trisodium salt	ChEBI
Nitrilotriacetic acid sodium salt	ChEBI
NTA trisodium salt	ChEBI
Trisodium aminotriacetate	ChEBI
Trisodium N,N-bis(carboxymethyl)glycinate	ChEBI
Trisodium nta	ChEBI
Nitrilotriacetate sodium salt	Generator
Trisodium aminotriacetic acid	Generator
Trisodium N,N-bis(carboxymethyl)glycinic acid	Generator
Trisodium nitrilotriacetic acid	Generator
Acid, nitrilotriacetic	MeSH
Aluminum nitrilotriacetate	MeSH
Nitrilotriacetate, aluminum	MeSH
Nitrilotriacetate, dysprosium	MeSH
Dysprosium nitrilotriacetate	MeSH
Nitrilotriacetate, trisodium	MeSH
Nitrilotriacetic acid	MeSH

Chemical Formula

C₆H₆NNa₃O₆

Average Mass

257.0842 Da

Monoisotopic Mass

256.98882 Da

IUPAC Name

trisodium 2-[bis(carboxylatomethyl)amino]acetate

Traditional Name

trisodium nitrilotriacetate

CAS Registry Number

Not Available

SMILES

[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O

InChI Identifier

InChI=1S/C6H9NO6.3Na/c8-4(9)1-7(2-5(10)11)3-6(12)13;;;/h1-3H2,(H,8,9)(H,10,11)(H,12,13);;;/q;3*+1/p-3

InChI Key

DZCAZXAJPZCSCU-UHFFFAOYSA-K

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Carboxylic acid salt
Tertiary amine
Tertiary aliphatic amine
Amino acid
Carboxylic acid
Organic alkali metal salt
Organic salt
Organic zwitterion
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Amine
Organic sodium salt
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.17	ALOGPS
logP	-2.1	ChemAxon
logS	-0.22	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	0	ChemAxon
Polar Surface Area	123.63 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.75 m³·mol⁻¹	ChemAxon
Polarizability	14.98 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010423

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21152

PDB ID

Not Available

ChEBI ID

132766

Good Scents ID

Not Available

References

General References

Iatropoulos MJ, Duan JD, Schmuck G, Williams GM: The urinary bladder carcinogen propoxur does not produce genotoxic effects in the urinary bladder of Wistar male rats. Exp Toxicol Pathol. 2015 Sep;67(9):453-8. doi: 10.1016/j.etp.2015.06.002. Epub 2015 Jul 8. [PubMed:26164753 ]
Malcolm AR, Mills LJ: Inhibition of gap-junctional intercellular communication between Chinese hamster lung fibroblasts by di(2-ethylhexyl) phthalate (DEHP) and trisodium nitrilotriacetate monohydrate (NTA). Cell Biol Toxicol. 1989 Jun;5(2):145-53. doi: 10.1007/BF00122649. [PubMed:2766028 ]
Kitahori Y, Shimoyama T, Ohshima M, Matsuki H, Hashimoto H, Minami S, Konishi N, Hiasa Y: Effects of trisodium nitrilotriacetate monohydrate, nitrilotriacetic acid and ammonium chloride on urinary bladder carcinogenesis in rats pretreated with N-bis(2-hydroxypropyl) nitrosamine. Cancer Lett. 1988 Dec 1;43(1-2):105-10. doi: 10.1016/0304-3835(88)90221-2. [PubMed:3203320 ]
Kitahori Y, Konishi N, Shimoyama T, Hiasa Y: Dose-dependent promoting effect of trisodium nitrilotriacetate monohydrate on urinary bladder carcinogenesis in Wistar rats pretreated with N-butyl-N-(4-hydroxybutyl)nitrosamine. Jpn J Cancer Res. 1985 Sep;76(9):818-22. [PubMed:3932279 ]

Showing NP-Card for Trisodium nitrilotriacetate (NP0338517)

MOL for NP0338517 (Trisodium nitrilotriacetate)

3D MOL for NP0338517 (Trisodium nitrilotriacetate)

3D SDF for NP0338517 (Trisodium nitrilotriacetate)

3D-SDF for NP0338517 (Trisodium nitrilotriacetate)

PDB for NP0338517 (Trisodium nitrilotriacetate)

3D PDB for NP0338517 (Trisodium nitrilotriacetate)

SMILES for NP0338517 (Trisodium nitrilotriacetate)

INCHI for NP0338517 (Trisodium nitrilotriacetate)

Structure for NP0338517 (Trisodium nitrilotriacetate)

3D Structure for NP0338517 (Trisodium nitrilotriacetate)