2-(4-aminoanilino)-5-nitrobenzenesulphonic acid

Short-term toxicity to aquatic invertebrates

Link to relevant study record(s)

Reference

Endpoint:

short-term toxicity to aquatic invertebrates

Type of information:

(Q)SAR

Adequacy of study:

weight of evidence

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

results derived from a valid (Q)SAR model and falling into its applicability domain, with limited documentation / justification

Justification for type of information:

The supporting QMRF report has been attached

Qualifier:

according to guideline

Guideline:

other: Refer below principle

Principles of method if other than guideline:

Prediction is done using QSAR Toolbox version 3.3 with log kow as the primary discriptors.

GLP compliance:

not specified

Specific details on test material used for the study:

Name of test material: 2-[(4-aminophenyl) amino]-5-nitrobenzenesulfonic acid
Molecular formula: C12H11N3O5S
Molecular weight: 309.301 g/mol
Physical Appearance: Solid
Smiles notation : O=S(=O)(O)c1c(Nc2ccc(N)cc2)ccc([N+]([O])=O)c1
InChl : GSITZZUEHIPPMH-UHFFFAOYSA-N

Analytical monitoring:

not specified

Vehicle:

not specified

Test organisms (species):

Daphnia magna

Test type:

static

Water media type:

saltwater

Total exposure duration:

48 h

Key result

Duration:

48 h

Dose descriptor:

EC50

Effect conc.:

109.81 mg/L

Nominal / measured:

estimated

Conc. based on:

test mat.

Basis for effect:

other: Intoxication

The prediction was based on dataset comprised from the following descriptors: EC50
Estimation method: Takes average value from the 5 nearest neighbours
Domain  logical expression:Result: In Domain

(((((((("a" or "b" or "c" )  and ("d" and ( not "e") )  )  and ("f" and ( not "g") )  )  and "h" )  and ("i" and ( not "j") )  )  and "k" )  and "l" )  and ("m" and "n" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Anilines (Acute toxicity) by US-EPA New Chemical Categories

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as SN1 AND SN1 >> Nitrenium Ion formation AND SN1 >> Nitrenium Ion formation >> Primary aromatic amine by DNA binding by OECD

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Strong binder, NH2 group by Estrogen Receptor Binding

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OASIS v.1.3

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >>  Michael-type addition, quinoid structures OR AN2 >>  Michael-type addition, quinoid structures >> Quinones OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Amino Anthraquinones OR Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide Side Chain OR Non-covalent interaction >> DNA intercalation >> Quinones OR Radical OR Radical >> Radical mechanism by ROS formation OR Radical >> Radical mechanism by ROS formation >> Polynitroarenes OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Amino Anthraquinones OR Radical >> Radical mechanism via ROS formation (indirect) >> Hydrazine Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitroaniline Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitroarenes with Other Active Groups OR Radical >> Radical mechanism via ROS formation (indirect) >> p-Aminobiphenyl Analogs OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones OR Radical >> Radical mechanism via ROS formation (indirect) >> Single-Ring Substituted Primary Aromatic Amines OR SN1 OR SN1 >> Nucleophilic attack after diazonium or carbenium ion formation OR SN1 >> Nucleophilic attack after diazonium or carbenium ion formation >> Nitroarenes with Other Active Groups OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Amino Anthraquinones OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> p-Aminobiphenyl Analogs OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Single-Ring Substituted Primary Aromatic Amines OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitroaniline Derivatives OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitroarenes with Other Active Groups OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Polynitroarenes OR SN2 OR SN2 >> SN2 attack on activated carbon Csp3 or Csp2 OR SN2 >> SN2 attack on activated carbon Csp3 or Csp2 >> Nitroarenes with Other Active Groups by DNA binding by OASIS v.1.3

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Strong binder, NH2 group by Estrogen Receptor Binding

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Moderate binder, NH2 group OR Non binder, impaired OH or NH2 group OR Non binder, non cyclic structure OR Weak binder, NH2 group OR Weak binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Bioavailable by Lipinski Rule Oasis ONLY

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as No alert found by Protein binding alerts for skin sensitization by OASIS v1.3

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> Direct acylation involving a leaving group OR Acylation >> Direct acylation involving a leaving group >> N-Acylsulfonamides  by Protein binding alerts for skin sensitization by OASIS v1.3

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Very fast by Bioaccumulation - metabolism half-lives ONLY

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Class 5 (Not possible to classify according to these rules) by Acute aquatic toxicity classification by Verhaar (Modified) ONLY

Domain logical expression index: "m"

Parametric boundary:The target chemical should have a value of log Kow which is >= -1.07

Domain logical expression index: "n"

Parametric boundary:The target chemical should have a value of log Kow which is <= -0.279

Validity criteria fulfilled:

not specified

Conclusions:

The short term toxicity on Daphnia magna (aquatic invertebrates) was predicted for 2-[(4-aminophenyl) amino]-5-nitrobenzenesulfonic acid using OECD QSAR toolbox version 3.3 and EC50 value was estimated to be 109.81 mg/l on Daphnia magna for 48 hrs duration considering Intoxication effects. Based on the value, 2-[(4-aminophenyl) amino]-5-nitrobenzenesulfonic acid (Cas no. 91-29-2) was likely to be non toxic to Daphnia magna (aquatic invertebrates), hence it can be considered to be not classified as per the CLP regulations.

Executive summary:

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the six closest read across substances, the short term toxicity on aquatic invertebrates was predicted for 2 -[(4-aminophenyl) amino]-5-nitrobenzenesulfonic acid (Cas no. 91-29-2). Effect concentration i.e EC50 value was estimated to be 109.81 mg/l for Daphnia magna for 48 hrs duration. Based on the effect value, 2 -[(4-aminophenyl) amino]-5-nitrobenzenesulfonic acid (Cas no. 91-29-2) was likely to be non toxic to aquatic invertebrates, hence it can be considered to be not classified as per the CLP classification criteria for aquatic environment.

Description of key information

Using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the six closest read across substances, the short term toxicity on aquatic invertebrates was predicted for 2 -[(4-aminophenyl) amino]-5-nitrobenzenesulfonic acid (Cas no. 91-29-2). Effect concentration i.e EC50 value was estimated to be 109.81 mg/l for Daphnia magna for 48 hrs duration. Based on the effect value, 2 -[(4-aminophenyl) amino]-5-nitrobenzenesulfonic acid (Cas no. 91-29-2) was likely to be non toxic to aquatic invertebrates, hence it can be considered to be not classified as per the CLP classification criteria for aquatic environment.

Key value for chemical safety assessment

Fresh water invertebrates

Fresh water invertebrates

Effect concentration:

109.81 mg/L

Additional information

Five studies including predicted data from validated tools and experimental data from authorative database for short term aquatic invertebrate’s endpoint of test chemical 2-[(4-aminophenyl) amino]-5-nitrobenzenesulfonic acid (Cas no. 91-29-2) with relevant read across which is close to target using log Kow as primary descriptor were summarised as follows:

 

First prediction using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the six closest read across substances, which indicate the short term toxicity on aquatic invertebrates was predicted for 2-[(4-aminophenyl) amino]-5-nitrobenzenesulfonic acid (Cas no. 91-29-2) and the Effect concentration i.e EC50 value was estimated to be 109.81mg/l for Daphnia magna for 48 hrs duration.

 

Similarly, prediction by EPI suite, ECOSAR version 1.1, on the basis of similarity of structure to chemicals for which the aquatic toxicity has been previously measured by structure-activity relationships (SARs) program suggest the LC 50 value for short term toxicity to aquatic invertebrates was predicted. On the basis of EPI suite, ECOSAR version 1.1, the LC 50 value for short term toxicity to aquatic invertebrates was predicted to be 47889.34 mg/l for 2-[(4-aminophenyl) amino]-5-nitrobenzenesulfonic acid in 48 hrs.

Above both predicted results of target are supported by experimental result of read across chemical 4-amino-N-pyrimidin-2-ylbenzenesulfonamide (Cas no.68-35-9) from authorative database i.e ECOTOX which suggest short term toxicity to aquatic invertebrates was performed in Daphnia magna (Water Flea) for 48 hrs with <24 hrs age and life stage Juvenile(s) with 2ND-5THBROOD Test in fresh water media with static condition. During the experiment, the EC50 value for 4-amino-N-pyrimidin-2-ylbenzenesulfonamide (Cas no. 68-35-9) was determined to be 212 mg/l on the basis of mobility.

One another read across (4-aminophenyl)arsonic acid (Cas no.98-50-0) from same data source i.e ECOTOX database indicate short term toxicity to aquatic invertebrates was performed in Daphnia magna (Water Flea) for 48 hrs with <24 hrs age.Test in fresh water media with static condition. During the experiment, the EC50 value for (4-aminophenyl)arsonic acid (Cas no.98-50-0) was determined to be 110 mg/l on the basis of mobility.

Last study also from ECOTOX database for read across sodium [(4-aminophenyl)sulfonyl](1,3-thiazol-2-yl)azanide (Cas no.144-74-1) indicate short term toxicity to aquatic invertebrates was performed in Daphnia magna (Water Flea) for 48 hrs with <24 hrs age.Test in fresh water media with static condition. During the experiment, the EC50 value for sodium [(4-aminophenyl)sulfonyl](1,3-thiazol-2-yl)azanide (Cas no.144-74-1) was determined to be 140.99 mg/l on the basis of mobility.

Thus based on the all available effect concentrations which is in the range of 109.81mg/l to 47889.34 mg/l for target and read across chemicals which come to the conclusion that test substance 2-[(4-aminophenyl) amino]-5-nitrobenzenesulfonic acid (Cas no. 91-29-2) was likely to be non toxic to aquatic invertebrates as it not exceed the classification criteria, hence it can be considered to be not classified as per the CLP regulation.