7-acetamido-4-hydroxy-3-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]naphthalene-2-sulphonic 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:

Data is from computational model developed by 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 the test material: 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid
- IUPAC name: 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid
- Molecular formula: C20H19N3O11S3
- Molecular weight: 573.578 g/mol
- Smiles: c1c(c(c(c2ccc(cc12)NC(=O)C)O)\N=N\c1ccc(cc1)S(=O)(=O)CCOS(=O)(=O)O)S(=O)(=O)O
-InChI:1S/C20H19N3O11S3/c1-12(24)21-15-4-7-17-13(10-15)11-18(36(28,29)30)19(20(17)25)23-22-14-2-5-16(6-3-14)35(26,27)9-8-34-37(31,32)33/h2-7,10-11,25H,8-9H2,1H3,(H,21,24)(H,28,29,30)(H,31,32,33)/b23-22+
- Substance type: Organic
- Physical state: Solid

Radiolabelling:

not specified

Test temperature:

25 deg.C

Analytical monitoring:

not specified

Key result

Type:

Koc

Value:

1 296 L/kg

Temp.:

25 °C

Remarks on result:

other: Log Koc= 3.1124 (estimated by MCI method)

Transformation products:

not specified

KOCWIN Program (v2.00) Results:

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

SMILES : O=C(Nc(ccc(c1cc(S(=O)(=O)O)c2N=Nc(ccc(S(=O)(=O)CCOS(=O)(=O)O)c3)c3)c2

O)c1)C

CHEM : 2-Naphthalenesulfonic acid, 7-(acetylamino)-4-hydroxy-3- 4- 2-(sulf

Koc may be sensitive to pH!

MOL FOR: C20 H19 N3 O11 S3

MOL WT : 573.57

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

Koc Estimate from MCI:

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

First Order Molecular Connectivity Index ........... : 17.065

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 9.4960

Fragment Correction(s):

1 N-CO-C (aliphatic carbon) ............ : -1.0277

1 Sulfone (-C-SO2-C-) ................. : -1.3136

1 Azo (-N=N-) ......................... : -0.6475

1 Sulfonic acid (-S(=O)-OH) ............. : -2.0000

1 Miscellaneous S(=O) group .......... : -1.2980

1 Aromatic Hydroxy (aromatic-OH) ....... : -0.0966

Corrected Log Koc .................................. : 3.1124

Estimated Koc: 1296 L/kg <===========

Validity criteria fulfilled:

not specified

Conclusions:

The Soil Adsorption Coefficient i.e. Koc value of test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid (CAS No. 68189-39-9) was estimated using EPI suite KOCWIN Program (v2.00) as 1296.0 L/kg (log Koc= 3.1124) by means of MCI method at 25 deg. C. This log Koc value indicates that test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid has moderate sorption to soil and therefore test chemical has slow migration potential to ground water.

Executive summary:

The Soil Adsorption Coefficient i.e. Koc value of test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid (CAS No. 68189-39-9) was estimated using EPI suite KOCWIN Program (v2.00) as 1296.0 L/kg (log Koc= 3.1124) by means of MCI method at 25 deg. C.  This log Koc value indicates that test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  has moderate sorption to soil and therefore test chemical has slow migration potential to ground water.

Description of key information

The Soil Adsorption Coefficient i.e. Koc value of test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid (CAS No. 68189-39-9) was estimated using EPI suite KOCWIN Program (v2.00) as 1296.0 L/kg (log Koc= 3.1124) by means of MCI method at 25 deg. C.  This log Koc value indicates that test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  has moderate sorption to soil and therefore test chemical has slow migration potential to ground water.

Key value for chemical safety assessment

Koc at 20 °C:

1 296

Additional information

Results of two predicted data studies for the target compound of 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid (CAS No. 68189-39-9) and supporting weight of evidence study for its read across chemical were reviewed for the Adsorption end point are summarized as below.

In first weight of evidence study of target chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid (CAS No. 68189-39-9) the Soil Adsorption Coefficient i.e. Koc value was estimated using Etimation Program Interface (EPI suite, 2017) KOCWIN Program (v2.00) as 1296.0 L/kg (log Koc= 3.1124) by means of MCI method at 25 deg. C.  This log Koc value indicates that test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  has moderate sorption to soil and therefore test chemical has slow migration potential to ground water.

 

Another weight of evidence study of target chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid(CAS no. 68189 -39 -9) was done 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 value was estimated to be7360.0L/kg (log Koc =3.8668) .The predicted KOC result was based on the 5 OECD principles. Thus based on the result it is concluded that the test substance7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acidhas a strong sorption to soil and sediment and therefore has negligible to slow migration potential to ground water.

 

Last weight of evidence study was done from Environmental Engineering and Management journal, 2007 for structurally similar read across chemical Acid Red 1 I this study it is stated that the adsorption of read across chemical on organo-clay is dominated by ion exchange process. The Freundlich and Langmuir adsorption isotherm constants of Acid Red 1 on organoclay are as follows: Acid Red 1 adsorption on organoclay the coefficients for fitting are 0.995 < rL2 < 0.997 and 0.573 < rF2 < 0.751. It can be seen that the Langmuir model yields a much better fit than the Freundlich model when the r2 values are compared. The affinity parameter, KL, and its reciprocal indicate that the adsorption capacity of Acid Red 1 on organoclay is highly perceptible to changes in temperature. The Qmax values indicate that Acid Red 1 possesses higher adsorption capacity at lower temperature.

 

On the basis of above results for target chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid (CAS No. 68189-39-9)(from EPI suite, ACD labs, Sci Finder database, Comptox chemistry dashboard and Chemspider 2017) and for its read across chemicals (From Environmental Engineering and Management journal) it can be concluded that the log Koc value of test 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acidranges from 3.1124 to 3.8668 indicating that the chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid has moderate to strong sorption to soil and sediment and therefore it has slow to negligible migration potential to ground water.

[LogKoc: 3.1124]