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

Endpoint summary

Description of key information

Biodegradation:

Biodegradation in water:

Biodegradbility of test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid was predicted by using OECD QSAR tool box v 3.3 using log Kow as primary descriptor. The test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid showed 1.7 % degradation by considering BOD as parameter and microrganisms as inoculum  in 28 days. Based on Percent biodegradability it is concluded that this test chemical is not readily biodegradable.

Biodegradation in water and sediments:

Estimation Programs Interface (EPI Suite, 2017) prediction model was run to predict the half-life in water and sediment for the test compound 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid (CAS No. 68189 -39 -9). If released in to the environment, 9.2 % of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of test chemical in water is estimated to be 60days (1440 hrs). The half-life (60 days estimated by EPI suite) indicates that the chemical is persistent in water and the exposure risk to aquatic animals is high whereas the half-life period of test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid in sediment is estimated to be 541.66 days (13000 hrs). However, as the percentage release of test chemical into the sediment is less than 1 % (i.e, reported as 0.792 %), indicates that test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid is not persistent in sediment.

Biodegradation in Soil:

The half-life period 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) in soil was estimated using Level III Fugacity Model by EPI Suite version 4.1 estimation database (EPI suite, 2017). If released into the environment, 90 % of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl] naphthalene-2-sulfonic acid in soil is estimated to be 120 days (2880 hrs). Based on this half-life value of test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4- [2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid, it is concluded that the chemical is not persistent in the soil environment and the exposure risk to soil dwelling animals is low .

Bioaccumulation:

Bioaccumulation:aquatic/sediments:

Using BCFBAF Program (v3.00) model of EPI suite (2017) the estimated bio concentration factor (BCF) for 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  (CAS No.68189-39-9) is 3.162L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000. Therefore it is concluded that test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  is non bioaccumulative in food chain.

Transport and Distribution:

Adsorption/desorption:

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.

Additional information

Biodegradation:

Biodegradation in water:

Results of two different predicted data study 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) and supporting experimental weight of evidence studies for its structurally similar read across chemical were summarized below.

In first weight of evidence study the biodegradability of test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid was predicted by using OECD QSAR tool box v3.3 using log Kow as primary descriptor in this study the test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid showed 1.7 % degradation by considering BOD as parameter and microrganisms as inoculum  in 28 days. Based on Percent biodegradability it is concluded that this test chemical is not readily biodegradable.

 

Another weight of evidence study was done by using Estimation Programs Interface Suite (EPI suite, 2017) to estimate the biodegradation potential of the test compound 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid (CAS no. 68189 -39 -9) in the presence of mixed populations of environmental microorganisms. The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI Linear Model, MITI Non-Linear Model and Anaerobic Model (called Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid is expected to be not readily biodegradable.

 

Next study was supporting weight of evidence study was done from Chemosphere journal, 1986 for structurally similar read across chemical 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4)( CAS no.17095-24-8). In this study the aerobic biodegradation experiment was performed for read across chemical by using activated sludge at concentration 0.5 g/L dry material as inoculums and initial concentration of chemical taken was 100mg/L for 28 days. By considering DOC removal parameter read across chemical showed     -53 % biodegradation in 28 days. This read across chemical was categorized in D category which shows no elimination in static test. This percentage value is also very less So it is concluded that read across chemical 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4) is not readily biodegradable.

 

Similarly, another supporting weight of evidence study was also done from Chemosphere journal, 1986 for another structurally similar read across chemical 2-Naphthalenesulfonic acid, 6-(acetylamino)-4-hydroxy-3-[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:2) ( CAS no.12225-88 -6) in this study the aerobic biodegradation experiment was performed for read across chemical using activated sludge at concentration 0.5 g/L dry material as inoculums and initial concentration of chemical taken was 100mg/L for 42 days. By considering DOC removal parameter test chemical showed 15 % degradation in 28 days and this read across chemical was categorized in D category which shows no elimination in static test. This percentage value is very less So it is concluded that read across chemical sodium 2-Naphthalenesulfonic acid, 6-(acetylamino)-4-hydroxy-3-[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:2) is not readily biodegradable.

 

Last supporting weight of evidence study was done from authoritative database J check, 2017 for structurally similar read across chemical 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4) (CAS no. 17095-24-8). In this study the read across chemical was subjected to biodegradation test by taking activated sludge as inoculums at 30 mg/L concentration. Biodegradation was analysed by using BOD, TOC and HPLC parameters. The initial concentration of test chemical was 100 mg/L. The study design used was of standard type. The read across chemical 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4) showed 4.0 % and 9 % biodegradation by considering BOD and TOC as parameter respectively but it showed 96 % biodegradation by HPLC parameter . Percent biodegradability values of read across chemical by BOD and TOC parameters are very low but by HPLC parameter test chemical showed very high biodegradability but this high value of biodegradation is not due complete degradation of read across chemical but it is due to partial change of test chemical and formation of 4-Amino-5-hydroxy-3,6-bis[4-(vinylsulfonyl)phenylazo]-2,7-naphthalenedisulfonic acid . Therefore on the basis of percent biodegradability by BOD and TOC parameters it is concluded that read across chemical 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4) is not readily biodegradable.

Results of all the studies mentioned above showed that the test chemical and structurally similar read across chemical are not readily biodegradable because percent biodegradability was very low in predicted studies as well as experimental studies. Therefore by compiling all above studies it is concluded that 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) can be considered as not readily biodegradable.

Biodegradation in water and sediments:

Estimation Programs Interface (EPI Suite, 2017) prediction model was run to predict the half-life in water and sediment for the test compound 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid (CAS No. 68189 -39 -9). If released in to the environment, 9.2 % of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of test chemical in water is estimated to be 60days (1440 hrs). The half-life (60 days estimated by EPI suite) indicates that the chemical is persistent in water and the exposure risk to aquatic animals is high whereas the half-life period of test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid in sediment is estimated to be 541.66 days (13000 hrs). However, as the percentage release of test chemical into the sediment is less than 1 % (i.e, reported as 0.792 %), indicates that test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid is not persistent in sediment.

Biodegradation in Soil:

The half-life period 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) in soil was estimated using Level III Fugacity Model by EPI Suite version 4.1 estimation database (EPI suite, 2017). If released into the environment, 90 % of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl] naphthalene-2-sulfonic acid in soil is estimated to be 120 days (2880 hrs). Based on this half-life value of test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4- [2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid, it is concluded that the chemical is not persistent in the soil environment and the exposure risk to soil dwelling animals is low.

Bioaccumulation:

Bioaccumulation:aquatic/sediments:

Various predicted data for the target compound 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 bioaccumulation end point which are summarized as below:

First weight of evidence studies 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) done by using BCFBAF Program (v3.00) model of Estimation Program Interface (EPI suite 2017) in this study the estimated bio concentration factor (BCF) for target chemical is 3.162L/kg wet-wt at 25 deg. c

 

Second weight of evidence study was done by Using Bio-concentration Factor (v12.1.0.50374) module of Advanced Chemistry Develpoment /I lab predictive module (2017) in this study the Bio-concentration Factor at range pH 1-14  of the 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) estimated to be 1.0 dimensionless.

Third weight of evidence study was done by using Scifinder database of American Chemical Society ( ACS, 2017) in this study the Bioconcentration factor (BCF) for test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid   was predicted in aquatic organisms by at pH 1-10 and temperature 25 °C .The Bioconcentration factor (BCF) of test substance at pH 1-10 and temperature 25 °C was estimated to be 1.0 dimensionless.  

 

Fourth weight of evidence study was done by using Chemspider- ACD/PhysChem Suite of Royal Society of Chemistry, 2017 in this study the Bioconcentration factor (BCF) for 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 predicted in aquatic organisms by  at pH 5.5 and pH 7.4. The Bioconcentration factor (BCF) of test chemical at pH 5.5 and pH 7.4 was estimated to be 1.0 dimensionless. 

 

Next study 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 bioaccumulation i.e BCF for test substance 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid was estimated to be 2.31 dimensionless. The predicted BCF result was based on the 5 OECD principles.

 

Last weight of evidence study was done for structurally similar read across chemical chemical 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4)(CAS no 17095-24-8) from authoritative database J check, 2017 in this study the Bioaccumulation test was conducted for 6 weeks for determination the bioconcentration factor (BCF) of read across chemical on test organism Cyprinus carpio. In this test Recovery ratio used was Test water: 1st concentration area: 98.4 %, 2nd concentration area : 95.4 %, Fish : 62.2 %, - Limit of detection : Test water 1st concentration area : 0.15 ppm, 2nd concentration area : 0.016 ppm, Fish : 2.1 ppm and

Nominal concentrations used in the study are 1st Concentration area: 2.0 mg/L, 2nd Concentration area: 0.2 mg/L and Range finding study was carried out on Rice fish (Oryzias latipes) TLm(48h) >= 1000 ppm(w/v). The lipid content of fish was 4.7 %.

Thus according to static Fish Test the BCF value 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4) was observed to be≤ 1.1 L/kg at dose concentration 2.0 mg/L and ≤ 11 L/kg at dose concentration 0.2 mg/L  on the basis of lipid content on test organism Cyprinus carpio during 6 weeks period. These BCF values indicate that the read across substance 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4) is not bioaccumulative in fish and food chain as these values are far less than 2000 criteria.

 

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  (from EPI suite, ACD labs, Sci Finder database, Chemspider and CompTox Chemistry Dashboard, 2017) and for its read across chemicals (From J check) it can be concluded that the BCF value of test substance 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  ranges from 1 to 3.162 dimensionless which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  is expected to be non bioaccumulative in the food chain.

Transport and Distribution:

Adsorption/desorption:

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.