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

Data is from OECD QSAR toolbox version.3.3 and QMRF report has been attached.

Qualifier:

according to guideline

Guideline:

other: Predicted data

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 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

Analytical monitoring:

not specified

Vehicle:

not specified

Test organisms (species):

Daphnia magna

Test type:

static

Water media type:

freshwater

Limit test:

no

Total exposure duration:

48 h

Key result

Duration:

48 h

Dose descriptor:

EC50

Effect conc.:

631.974 mg/L

Nominal / measured:

estimated

Conc. based on:

test mat.

Basis for effect:

other: Intoxication

Remarks on result:

other: not toxic

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" or "d" )  and ("e" and ( not "f") )  )  and ("g" and ( not "h") )  )  and ("i" and ( not "j") )  )  and ("k" and ( not "l") )  )  and ("m" and ( not "n") )  )  and ("o" and ( not "p") )  )  and ("q" and ( not "r") )  )  and ("s" and ( not "t") )  )  and "u" )  and "v" )  and "w" )  and ("x" and ( not "y") )  )  and "z" )  and ("aa" and "ab" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Vinyl Sulfones by US-EPA New Chemical Categories

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Ester aminolysis AND Acylation >> Ester aminolysis >> Amides by Protein binding by OASIS v1.3

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Direct Acylation Involving a Leaving group AND Acylation >> Direct Acylation Involving a Leaving group >> Acetates by Protein binding by OECD

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Acid moiety AND Amides AND Phenol Amines AND Phenols by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "e"

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

Domain logical expression index: "f"

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 AN2 >> Michael-type addition on alpha, beta-unsaturated carbonyl compounds OR AN2 >> Michael-type addition on alpha, beta-unsaturated carbonyl compounds >> Four- and Five-Membered Lactones OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation >> Geminal Polyhaloalkane Derivatives OR AN2 >> Shiff base formation after aldehyde release OR AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters OR AN2 >> Shiff base formation for aldehydes OR AN2 >> Shiff base formation for aldehydes >> Geminal Polyhaloalkane Derivatives OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Coumarins OR Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide Side Chain OR Non-covalent interaction >> DNA intercalation >> Quinones OR Non-specific OR Non-specific >> Incorporation into DNA/RNA, due to structural analogy with  nucleoside bases    OR Non-specific >> Incorporation into DNA/RNA, due to structural analogy with  nucleoside bases    >> Specific Imine and Thione Derivatives OR Radical OR Radical >> Generation of reactive oxygen species OR Radical >> Generation of reactive oxygen species >> Thiols OR Radical >> Generation of ROS by glutathione depletion (indirect) OR Radical >> Generation of ROS by glutathione depletion (indirect) >> Haloalkanes Containing Heteroatom 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) >> Coumarins OR Radical >> Radical mechanism via ROS formation (indirect) >> Geminal Polyhaloalkane Derivatives 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) >> Quinones OR Radical >> Radical mechanism via ROS formation (indirect) >> Specific Imine and Thione Derivatives OR SN1 OR SN1 >> Carbenium ion formation OR SN1 >> Carbenium ion formation >> Alpha-Haloethers OR SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> Specific Acetate Esters 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 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 SN1 >> Nucleophilic substitution on diazonium ions OR SN1 >> Nucleophilic substitution on diazonium ions >> Specific Imine and Thione Derivatives OR SN2 OR SN2 >> Acylation OR SN2 >> Acylation >> Specific Acetate Esters OR SN2 >> Acylation involving a leaving group  OR SN2 >> Acylation involving a leaving group  >> Geminal Polyhaloalkane Derivatives OR SN2 >> Acylation involving a leaving group after metabolic activation OR SN2 >> Acylation involving a leaving group after metabolic activation >> Geminal Polyhaloalkane Derivatives OR SN2 >> Alkylation, ring opening SN2 reaction OR SN2 >> Alkylation, ring opening SN2 reaction >> Four- and Five-Membered Lactones OR SN2 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Coumarins OR SN2 >> Direct acting epoxides formed after metabolic activation >> Quinoline Derivatives OR SN2 >> DNA alkylation OR SN2 >> DNA alkylation >> Alkylphosphates, Alkylthiophosphates and Alkylphosphonates OR SN2 >> DNA alkylation >> Vicinal Dihaloalkanes OR SN2 >> Internal SN2 reaction with aziridinium and/or cyclic sulfonium ion formation (enzymatic) OR SN2 >> Internal SN2 reaction with aziridinium and/or cyclic sulfonium ion formation (enzymatic) >> Vicinal Dihaloalkanes OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Haloalkanes Containing Heteroatom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Specific Acetate Esters OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation >> Geminal Polyhaloalkane Derivatives OR SN2 >> SN2 at an activated carbon atom OR SN2 >> SN2 at an activated carbon atom >> Quinoline Derivatives OR SN2 >> SN2 at sp3-carbon atom OR SN2 >> SN2 at sp3-carbon atom >> Alpha-Haloethers 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: "g"

Referential boundary: The target chemical should be classified as Not possible to classify according to these rules by DPRA Cysteine peptide depletion

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Moderate reactive OR Moderate reactive >> Five-membered heterocyclic urea by DPRA Cysteine peptide depletion

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Non binder, MW>500 by Estrogen Receptor Binding

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Very strong binder, OH group OR Weak binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Ester aminolysis AND Acylation >> Ester aminolysis >> Amides by Protein binding by OASIS v1.3

Domain logical expression index: "l"

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

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Ester aminolysis AND Acylation >> Ester aminolysis >> Amides by Protein binding by OASIS v1.3

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as SN2 >> Nucleophilic substitution at sp3 carbon atom >> alpha-Activated haloalkanes  by Protein binding by OASIS v1.3

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Ester aminolysis AND Acylation >> Ester aminolysis >> Amides by Protein binding by OASIS v1.3

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as Nucleophilic addition by Protein binding by OASIS v1.3

Domain logical expression index: "q"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Direct Acylation Involving a Leaving group AND Acylation >> Direct Acylation Involving a Leaving group >> Acetates by Protein binding by OECD

Domain logical expression index: "r"

Referential boundary: The target chemical should be classified as Acylation >> Direct Acylation Involving a Leaving group >> Azlactone by Protein binding by OECD

Domain logical expression index: "s"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Direct Acylation Involving a Leaving group AND Acylation >> Direct Acylation Involving a Leaving group >> Acetates by Protein binding by OECD

Domain logical expression index: "t"

Referential boundary: The target chemical should be classified as Acylation >> Isocyanates and Related Chemicals OR Acylation >> Isocyanates and Related Chemicals >> Thiocyanates-Acylation OR Michael addition OR Michael addition >> Polarised Alkenes OR Michael addition >> Polarised Alkenes >> Polarised alkene - ketones OR No alert found OR SN2 OR SN2 >> SN2 reaction at a sulphur atom OR SN2 >> SN2 reaction at a sulphur atom >> Thiocyanates-SN2 OR SN2 >> SN2 reaction at sp3 carbon atom OR SN2 >> SN2 reaction at sp3 carbon atom >> Allyl acetates and related chemicals by Protein binding by OECD

Domain logical expression index: "u"

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: "v"

Referential boundary: The target chemical should be classified as Reactive unspecified by Acute aquatic toxicity MOA by OASIS ONLY

Domain logical expression index: "w"

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

Domain logical expression index: "x"

Referential boundary: The target chemical should be classified as Not known precedent reproductive and developmental toxic potential by DART scheme v.1.0

Domain logical expression index: "y"

Referential boundary: The target chemical should be classified as Known precedent reproductive and developmental toxic potential OR Toluene and small alkyl toluene derivatives (8a) by DART scheme v.1.0

Domain logical expression index: "z"

Referential boundary: The target chemical should be classified as Aryl AND Azo AND Carboxamide AND Fused carbocyclic aromatic AND Naphtalene AND Phenol AND Sulfate AND Sulfone AND Sulfonic acid by Organic Functional groups ONLY

Domain logical expression index: "aa"

Parametric boundary:The target chemical should have a value of log Kow which is >= -4.44

Domain logical expression index: "ab"

Parametric boundary:The target chemical should have a value of log Kow which is <= 1.5

Conclusions:

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the toxicity to invertebrate was predicted 7-acetamido-4-hydroxy-3-[(4-{[2-(sulfooxy)ethyl]sulfonyl}phenyl)diazenyl]naphthalene-2-sulfonic acid (CAS: 68189-39-9). Intoxication value was estimated to be 631.974 mg/l for Daphnia magna for 48 hrs duration. It was concluded that 7-acetamido-4-hydroxy-3-[(4-{[2-(sulfooxy)ethyl]sulfonyl}phenyl)diazenyl]naphthalene-2-sulfonic acid (CAS: 68189-39-9) was likely to be not toxic to aquatic invertebrate.

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 closest read across substances, the toxicity to invertebrate was predicted 7-acetamido-4-hydroxy-3-[(4-{[2-(sulfooxy)ethyl]sulfonyl}phenyl)diazenyl]naphthalene-2-sulfonic acid (CAS: 68189-39-9). Intoxication value was estimated to be 631.974 mg/l for Daphnia magna for 48 hrs duration. It was concluded that 7-acetamido-4-hydroxy-3-[(4-{[2-(sulfooxy)ethyl]sulfonyl}phenyl)diazenyl]naphthalene-2-sulfonic acid (CAS: 68189-39-9) was likely to be not toxic to aquatic invertebrate.

Description of key information

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the toxicity to invertebrate was predicted 7-acetamido-4-hydroxy-3-[(4-{[2-(sulfooxy)ethyl]sulfonyl}phenyl)diazenyl]naphthalene-2-sulfonic acid (CAS: 68189-39-9). Intoxication value was estimated to be 631.974 mg/l for Daphnia magna for 48 hrs duration. It was concluded that 7-acetamido-4-hydroxy-3-[(4-{[2-(sulfooxy)ethyl]sulfonyl}phenyl)diazenyl]naphthalene-2-sulfonic acid (CAS: 68189-39-9) was likely to be not toxic to aquatic invertebrate.

Key value for chemical safety assessment

Fresh water invertebrates

Fresh water invertebrates

Effect concentration:

631.974 mg/L

Additional information

Following studies include predicted data and the experimental studies for the structurally similar read across to conclude the toxicity extent of 7-acetamido-4-hydroxy-3-[(4-{[2-(sulfooxy)ethyl]sulfonyl}phenyl)diazenyl]naphthalene-2-sulfonic acid (CAS: 68189-39-9) towards aquatic invertebrate is summarized as follows:

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the toxicity to invertebrate was predicted 7-acetamido-4-hydroxy-3-[(4-{[2-(sulfooxy)ethyl]sulfonyl}phenyl)diazenyl]naphthalene-2-sulfonic acid (CAS: 68189-39-9). Intoxication value was estimated to be 631.974 mg/l for Daphnia magna for 48 hrs duration. It was concluded that 7-acetamido-4-hydroxy-3-[(4-{[2-(sulfooxy)ethyl]sulfonyl}phenyl)diazenyl]naphthalene-2-sulfonic acid (CAS: 68189-39-9) was likely to be not toxic to aquatic invertebrate.

The predicted data for the target chemical is supported by the experimental study of structurally similar read across disodium 5-acetamido-4-hydroxy-3-(phenyldiazenyl)naphthalene-2,7-disulfonate (CAS: 3734 -67 -6) from ABITEC reports suggests that To study the effects of Acid Red 1 (Red 2G); disodium 5-acetamido-4-hydroxy-3-(phenyldiazenyl)naphthalene-2,7-disulfonate on aquatic invertebrate test was carried out according to the OECD Guideline 202 (Daphnia sp. Acute Immobilisation Test).

The solution 100 mg/L was prepared by dissolving red powder in reconstituted water. The solution was kept 30 min in ultrasonic bath.

The study was carried out with 5 daphnia magna per vessel under static condition at temp 18°C, pH of 8.2, dissolved oxygen 7.6 mg/L and above at end of test, the inhibition of mobility of daphnids was determined during the test.

The effective concentration EC50 to 50% of daphnia magna for Disodium 5-acetylamino-4-hydroxy-3-(phenylazo)naphthalene-2,7-disulphonate in 48 hr is 100 mg/L. It can be concluded from the value that the Disodium 5-acetylamino-4-hydroxy-3-(phenylazo)naphthalene-2,7-disulphonate is not toxic to the aquatic invertebrate and can be considered as "not classified" as per the classification crietria fro aquatic environment.

Similar experimental study of another structurally similar read across Tetrasodium 4-amino-5-hydroxy-3,6-bis[[4-[[2-(sulphonatooxy)ethyl]sulphonyl]phenyl]azo]naphthalene-2,7-disulphonate (CAS: 17095 -24 -8) from Authoritative database J-Check also assists that the Short-term toxicity to aquatic invertebrates test was carried out according to the OECD Guideline 202 (Daphnia sp. Acute Immobilisation Test)to study the effects ofTetrasodium 4-amino-5-hydroxy-3,6-bis[[4-[[2-(sulphonatooxy)ethyl]sulphonyl]phenyl]azo]naphthalene-2,7-disulphonate on aquatic invertebrate.

Mobility of 50% population of daphnia magna was measured during the test. The effective concentration EC50 to 50% population of daphnia magna for Tetrasodium 4-amino-5-hydroxy-3,6-bis[[4-[[2-(sulphonatooxy)ethyl]sulphonyl]phenyl]azo]naphthalene-2,7-disulphonate on aquatic invertebrate in 48 hr is >1000 mg/L. It can be concluded from the value that the Tetrasodium 4-amino-5-hydroxy-3,6-bis[[4-[[2-(sulphonatooxy)ethyl]sulphonyl]phenyl]azo]naphthalene-2,7-disulphonate is not toxic to the aquatic invertebrate and can be considered as “not classified” as per the classification criteria for aquatic environment.

Thus based on the effect concentrations which is in range of 100 mg/l to >1000 mg/L gives the conclusion that test substance 7-acetamido-4-hydroxy-3-[(4-{[2-(sulfooxy)ethyl]sulfonyl}phenyl)diazenyl]naphthalene-2-sulfonic acid (CAS: 68189-39-9) was likely to be not toxic to invertebrate at environmentally relevant concentrations and applying weight of evidence approach it can be considered to be“not classified”as per the CLP classification criteria for aquatic environment.