NP-MRD: Showing NP-Card for edetic acid (NP0222808)

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Record Information

Version

2.0

Created at

2022-09-06 00:44:16 UTC

Updated at

2022-09-06 00:44:17 UTC

NP-MRD ID

NP0222808

Secondary Accession Numbers

None

Natural Product Identification

Common Name

edetic acid

Description

Edetic Acid, also known as EDTA or edetate, belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Edetic Acid is a drug which is used for the reduction of blood levels and depot stores of lead in lead poisoning (acute and chronic) and lead encephalopathy, in both pediatric populations and adults. Edetic Acid is a very strong basic compound (based on its pKa). Edetic Acid is a potentially toxic compound. edetic acid is found in Apis cerana. In addition to having a lower toxicity after chelation, IDS is degraded by Agrobacterium tumefaciens (BY6), which can be harvested on a large scale.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
    1.8165    2.6947   -0.8617 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7793    2.2712   -0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6222    3.1903    0.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    0.8147   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9397    0.0700   -0.6678 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7058    0.1446    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4198   -0.5815   -0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873   -0.4943    0.0086 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7421   -1.1395   -0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0604   -1.0117   -0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4378   -0.3497    0.9543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1471   -1.7421   -0.6258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8571    0.3536    1.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535    1.6053    0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7802    1.7742   -0.5422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9515    2.5656    1.6178 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786   -1.1693   -1.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7589   -2.1778   -0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1910   -3.2849   -0.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6684   -1.9749    1.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7088    4.1311   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9897    0.6014   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1704    0.5399    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702   -0.3383    1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4894    1.2004    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248   -0.1915   -1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -1.6747   -0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7915   -0.8012   -1.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4978   -2.2550   -0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1601   -1.6608   -1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119    0.5905    1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806   -0.1208    1.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2119    2.9985    2.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977   -1.6412   -1.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3211   -0.9617   -1.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4160   -1.9752    1.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  5 17  1  0
 17 18  1  0
 18 20  1  0
 18 19  2  0
  8 13  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 12 30  1  0
  9 28  1  0
  9 29  1  0
  7 26  1  0
  7 27  1  0
  6 24  1  0
  6 25  1  0
  4 22  1  0
  4 23  1  0
  3 21  1  0
 17 34  1  0
 17 35  1  0
 20 36  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
M  END


  Mrv1652304032018332D          

 20 19  0  0  0  0            999 V2000
    2.4453    0.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5254    1.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7955   -0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950   -1.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854    1.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6056    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6351   -2.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0149   -0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2554    0.4677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -0.6236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752    1.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2554    2.6505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1457   -0.6236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8757    0.7796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4453   -1.8709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -2.8064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2552   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5252    0.4677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  1  1  0  0  0  0
 11  3  1  0  0  0  0
 11  4  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 14  7  1  0  0  0  0
 15  8  2  0  0  0  0
 16  8  1  0  0  0  0
 17  9  2  0  0  0  0
 18  9  1  0  0  0  0
 19 10  2  0  0  0  0
 20 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222808

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
KCXVZYZYPLLWCC-UHFFFAOYSA-N

> <FORMULA>
C10H16N2O8

> <MOLECULAR_WEIGHT>
292.2426

> <EXACT_MASS>
292.090665498

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.63729533041365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetic acid

> <ALOGPS_LOGP>
-1.25

> <JCHEM_LOGP>
-4.924670289588847

> <ALOGPS_LOGS>
-1.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.898133077693589

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.349928817402512

> <JCHEM_PKA_STRONGEST_BASIC>
7.728016348707842

> <JCHEM_POLAR_SURFACE_AREA>
155.68

> <JCHEM_REFRACTIVITY>
62.345600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
edta

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0       4.565   0.582   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.060  -0.873   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.581   2.328   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.085  -0.291   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.044  -2.619   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.573   3.492   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.597   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.052  -3.783   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.028  -0.291   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.077   0.873   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       2.548  -1.164   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       4.060   3.201   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.077   4.948   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       9.605  -1.164   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.101   1.455   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.565  -3.492   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.548  -5.239   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.476  -1.746   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.980   0.873   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1   12                                                       
CONECT    3    7   11                                                       
CONECT    4    8   11                                                       
CONECT    5    9   12                                                       
CONECT    6   10   12                                                       
CONECT    7    3   13   14                                                  
CONECT    8    4   15   16                                                  
CONECT    9    5   17   18                                                  
CONECT   10    6   19   20                                                  
CONECT   11    1    3    4                                                  
CONECT   12    2    5    6                                                  
CONECT   13    7                                                            
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   10                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
(Ethylenedinitrilo)tetraacetic acid, ion(4-)	ChEBI
2,2',2'',2'''-(ethane-1,2-diyldinitrilo)tetraacetate	ChEBI
Acide edetique	ChEBI
Acide ethylenediaminetetracetique	ChEBI
Acido edetico	ChEBI
Acidum edeticum	ChEBI
EDTA	ChEBI
EDTA, ion(4-)	ChEBI
Ethylenediaminetetraacetate	ChEBI
H4EDta	ChEBI
N,N'-1,2-ethane diylbis-(N-(carboxymethyl)glycine)	ChEBI
{[-(bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetIC ACID	ChEBI
Ethylenediaminetetraacetic acid	Kegg
Versene acid	Kegg
(Ethylenedinitrilo)tetraacetate, ion(4-)	Generator
2,2',2'',2'''-(ethane-1,2-diyldinitrilo)tetraacetic acid	Generator
{[-(bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetate	Generator
Edetate	Generator
CaEDTA	HMDB
Calcium disodium edetate	HMDB
Calcium disodium versenate	HMDB
Edetate calcium	HMDB
Edetate calcium disodium	HMDB
EDT	HMDB
Acid, ethylenedinitrilotetraacetic	HMDB
Calcium tetacine	HMDB
Copper edta	HMDB
EDTA, disodium	HMDB
EDTA, distannous	HMDB
Edathamil	HMDB
Edetates	HMDB
Edetic acid, dipotassium salt	HMDB
Edetic acid, disodium salt, dihydrate	HMDB
Edetic acid, disodium, magnesium salt	HMDB
Edetic acid, magnesium salt	HMDB
Ethylenedinitrilotetraacetic acid	HMDB
N,N'-1,2-ethanediylbis(N-(carboxymethyl)glycine)	HMDB
Potassium edta	HMDB
Chromium edta	HMDB
Coprin	HMDB
Dinitrilotetraacetate, ethylene	HMDB
Disodium ethylene dinitrilotetraacetate	HMDB
Distannous edta	HMDB
EDTA, chromium	HMDB
EDTA, dicobalt	HMDB
EDTA, gallium	HMDB
EDTA, magnesium disodium	HMDB
Edetate disodium calcium	HMDB
Edetic acid, disodium salt	HMDB
Edetic acid, monosodium salt	HMDB
Edetic acid, potassium salt	HMDB
Gallium edta	HMDB
Tetacine, calcium	HMDB
Versene	HMDB
Acid, ethylenediaminetetraacetic	HMDB
Calcitetracemate, disodium	HMDB
Chelaton 3	HMDB
Dinitrilotetraacetate, disodium ethylene	HMDB
Disodium edta	HMDB
EDTA, copper	HMDB
Edetic acid, sodium salt	HMDB
Ethylene dinitrilotetraacetate, disodium	HMDB
Stannous edta	HMDB
Tetracemate	HMDB
Versenate	HMDB
Versenate, calcium disodium	HMDB
Acid, edetic	HMDB
Dicobalt edta	HMDB
Disodium calcitetracemate	HMDB
Disodium versenate, calcium	HMDB
EDTA, potassium	HMDB
EDTA, stannous	HMDB
Edetate, calcium disodium	HMDB
Edetic acid, calcium salt	HMDB
Edetic acid, calcium, sodium salt	HMDB
Edetic acid, chromium salt	HMDB
Edetic acid, disodium, monopotassium salt	HMDB
Edetic acid, monopotassium salt	HMDB
Ethylene dinitrilotetraacetate	HMDB
Magnesium disodium edta	HMDB
Edetic acid	ChEBI

Chemical Formula

C₁₀H₁₆N₂O₈

Average Mass

292.2426 Da

Monoisotopic Mass

292.09067 Da

IUPAC Name

2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetic acid

Traditional Name

edta

CAS Registry Number

Not Available

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 Key

KCXVZYZYPLLWCC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

ethylenediamine derivative (CHEBI:42191 )
polyamino carboxylic acid (CHEBI:42191 )
tetracarboxylic acid (CHEBI:42191 )

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	-1.2	ALOGPS
logP	-4.9	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	2.35	ChemAxon
pKa (Strongest Basic)	7.73	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	155.68 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	62.35 m³·mol⁻¹	ChemAxon
Polarizability	25.64 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