Pyridine-2,4-dicarboxylic acid

Adsorption / desorption

Link to relevant study record(s)

Reference

Endpoint:

adsorption / desorption

Remarks:

adsorption

Type of information:

calculation (if not (Q)SAR)

Adequacy of study:

weight of evidence

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Justification for type of information:

Estimated data generated using the EPI Suite model developed by the USEPA.

Qualifier:

according to guideline

Guideline:

other: Modeling database

Principles of method if other than guideline:

Prediction done using KOCWIN Program (v2.00)

GLP compliance:

not specified

Type of method:

other: MCI Method

Media:

soil

Specific details on test material used for the study:

- Name of test material (IUPAC name): 2,4-Pyridinedicarboxylic acid
- Common name: Pyridine-2,4-dicarboxylic acid
- Molecular formula: C7H5NO4
- Molecular weight: 167.12 g/mol
- Smiles notation: c1(cc(ncc1)C(O)=O)C(O)=O
- InChl: 1S/C7H5NO4/c9-6(10)4-1-2-8-5(3-4)7(11)12/h1-3H,(H,9,10)(H,11,12)
- Substance type: Organic
- Physical state: Solid

Radiolabelling:

not specified

Test temperature:

25 deg.C

Analytical monitoring:

not specified

Key result

Type:

Koc

Value:

38.98 L/kg

Temp.:

25 °C

Remarks on result:

other: Log Koc= 1.5909 (estimated by MCI method)

Transformation products:

not specified

KOCWIN Program (v2.00) Results:

==============================

SMILES : O=C(O)c(ccnc1C(=O)O)c1

CHEM : 2,4-Pyridinedicarboxylic acid

MOL FOR: C7 H5 N1 O4

Koc may be sensitive to pH!

--------------------------- KOCWIN v2.00 Results ---------------------------

Koc Estimate from MCI:

---------------------

First Order Molecular Connectivity Index ........... : 5.609

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 3.5238

Fragment Correction(s):

* Organic Acid (-CO-OH) ............... : -1.6249

1 Pyridine ring ......................... : -0.3080

Corrected Log Koc .................................. : 1.5909

Estimated Koc: 38.98 L/kg <===========

Validity criteria fulfilled:

not specified

Conclusions:

The soil adsorption coefficient i.e Koc value of 2,4-Pyridinedicarboxylic acid was estimated to be 38.98 L/kg (log Koc=1.5909) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 2,4-Pyridinedicarboxylic acid has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

Executive summary:

KOCWIN model (v2.00) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the soil adsorption coefficient i.e Koc value of test chemical 2,4-Pyridinedicarboxylic acid (CAS No. 499 -80 -9). The soil adsorption coefficient i.e Koc value of 2,4-Pyridinedicarboxylic acid was estimated to be 38.98 L/kg (log Koc=1.5909)  by means of MCI method (at 25 deg C). This Koc value indicates that the substance 2,4-Pyridinedicarboxylic acid has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

Description of key information

KOCWIN model (v2.00) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the soil adsorption coefficient i.e Koc value of test chemical2,4-Pyridinedicarboxylic acid(CAS No. 499 -80 -9).The soil adsorption coefficient i.e Koc value of 2,4-Pyridinedicarboxylic acid was estimated to be 38.98 L/kg (log Koc=1.5909)  by means of MCI method (at 25 deg C). This Koc value indicates that the substance 2,4-Pyridinedicarboxylic acid has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

Key value for chemical safety assessment

Koc at 20 °C:

38.98

Additional information

Various predicted data for the target compound 2,4-Pyridinedicarboxylic acid (CAS No. 499-80-9) and supporting weight of evidence study for its structurally similar read across substance were reviewed for the adsorption end point which are summarized as below:

 

In aprediction done using theKOCWIN Program(v2.00) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the soil adsorption coefficient i.e Koc value of test chemical 2,4-Pyridinedicarboxylic acid (CAS No. 499 -80 -9). The soil adsorption coefficient i.e Koc value of 2,4-Pyridinedicarboxylic acid was estimated to be 38.98 L/kg (log Koc=1.5909)  by means of MCI method (at 25 deg C). This Koc value indicates that the substance 2,4-Pyridinedicarboxylic acid has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

The Soil Adsorption Coefficient i.e Koc value of test substance 2,4-Pyridinedicarboxylic acid was estimated using Adsorption Coefficient module (v12.1.0.50374) program as Koc 9.89, 14.3, 11.2, 3.16 and 1 at pH range 0, 1, 2, 3 and 4-14 respectively (log Koc ranges from  0 to 1.2 ± 1.0)(ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017). This Koc value indicates that the test substance 2,4-Pyridinedicarboxylic acid has a negligible sorption to soil and therefore have rapid migration potential to groundwater.

 

In an another prediction done by using ChemSpider Database (2017),the Soil Adsorption Coefficient i.e Koc value of test substance 2,4-Pyridinedicarboxylic acid (CAS no. 499 -80 -9) was estimated using ChemSpider Database. The adsorption coefficient (Koc) value of substance 2,4-Pyridinedicarboxylic acid was estimated to be 1 (Log Koc = 0) at pH 5.5 and 7.4, respectively. This Koc value indicates that the test substance 2,4-Pyridinedicarboxylic acid has a negligible sorption to soil and therefore have rapid migration potential to groundwater.

 

Additional soil adsorption coefficient i.e Koc value of test chemical2,4-Pyridinedicarboxylic acid (CAS No. 499 -80 -9)was estimated using the SciFinder database (American Chemical Society (ACS), 2017). The soil adsorption coefficient i.e Koc value of 2,4-Pyridinedicarboxylic acid was estimated to be 9.42, 7.39, 2.08 and 1 at pH range 1, 2, 3 and 4-10, respectively (log Koc value ranges from 0 to 0.974) (at 25 deg C). This Koc value indicates that the substance  2,4-Pyridinedicarboxylic acid has a negligible sorption to soil and sediment and therefore have rapid migration potential to ground water.

 

From CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application)  V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical), the adsorption coefficient i.e KOC for test substance 2,4-Pyridinedicarboxylic acid was estimated to be 117 L/kg (log Koc = 2.068).The predicted KOC result based on the 5 OECD principles. This Koc value indicates that the substance 2,4-Pyridinedicarboxylic acid has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

In a supporting weight of evidence study from authoritative database (HSDB, 2017) for the read across chemical 2,3-Pyridinedicarboxylic acid (CAS no. 89-00-9),adsorption study was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 2,3-Pyridinedicarboxylic acid. The adsorption coefficient (Koc) value was calculated using a water solubility of 11000 mg/l and a regression derived equation. The adsorption coefficient (Koc) value of test substance 2,3-Pyridinedicarboxylic acid was estimated to be 26 (Log Koc = 1.414). This Koc value indicates that the substance 2,3-Pyridinedicarboxylic acid has a negligible sorption to soil and sediment and therefore have rapid migration potential to ground water.

 

For the read across chemical 1,3-benzenedicarboxylic acid (CAS no. 121-91-5),adsorption study was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 1,3-benzenedicarboxylic acid (HSDB, 2017). The adsorption coefficient (Koc) value was calculated using astructure estimation method based on molecular connectivity indices. The adsorption coefficient (Koc) value of test substance 1,3-benzenedicarboxylic acid was estimated to be 79 (Log Koc = 1.897). This Koc value indicates that the substance 1,3-benzenedicarboxylic acid has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

On the basis of above overall results for target chemical2,4-Pyridinedicarboxylic acid(from EPI suite, ACD labs,ChemSpider and CompTox Chemistry Dashboard,2017) and for its read across substance from authoritative database (HSDB, 2017), it can be concluded that the Koc value of test substance2,4-Pyridinedicarboxylic acidranges from 1–117,indicating that the test chemical2,4-Pyridinedicarboxylic acidhas a negligible to low sorption to soil and sediment and therefore have rapid to moderate migration potential to ground water.

[LogKoc: 1.5909]