7-benzamido-4-hydroxynaphthalene-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:

The supporting QMRF report has been attached

Qualifier:

according to guideline

Guideline:

other: as mentioned below

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: 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid
- Molecular formula: C17 H13 N O5 S
- Molecular weight: 343.3577 g/mol
- Smiles notation: c1ccc(cc1)C(=O)Nc2ccc3c(c2)cc(cc3O)S(=O)(=O)O
- InChl: 1S/C17H13NO5S/c19-16-10-14(24(21,22)23)9-12-8-13(6-7-15(12)16)18-17(20)11-4-2-1-3-5-11/h1-10,19H,(H,18,20)(H,21,22,23)
- Substance type: Organic
- Physical state: Solid

Test organisms (species):

Daphnia magna

Test type:

static

Water media type:

freshwater

Total exposure duration:

48 h

Hardness:

126-166 mg/l CaCO3

Test temperature:

20.0 ± 1°C

Duration:

48 h

Dose descriptor:

EC50

Effect conc.:

840.24 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" or "d" or "e" or "f" )  and ("g" and ( not "h") )  )  and ("i" and ( not "j") )  )  and ("k" and ( not "l") )  )  and "m" )  and "n" )  and ("o" and ( not "p") )  )  and ("q" and "r" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Non-covalent interaction AND Non-covalent interaction >> DNA intercalation AND Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide Side Chain by DNA binding by OASIS v.1.3

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Low reactive AND Low reactive >> N-substituted aromatic amides by DPRA Cysteine peptide depletion

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Low reactive AND Low reactive >> N-substituted aromatic amides by DPRA Lysine peptide depletion

Domain logical expression index: "d"

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

Domain logical expression index: "e"

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: "f"

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: "g"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OECD

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> P450 Mediated Activation to Acyl Halides OR Acylation >> P450 Mediated Activation to Acyl Halides >> 1,1-Dihaloalkanes OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates >> Benzylamines-Acylation OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates >> Formamides OR Michael addition OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Alkyl phenols OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Arenes OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Hydroquinones OR Michael addition >> Polarised Alkenes-Michael addition OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated esters OR Michael addition >> Quinones and Quinone-type Chemicals OR Michael addition >> Quinones and Quinone-type Chemicals >> Quinones OR Schiff base formers OR Schiff base formers >> Chemicals Activated by P450 to Glyoxal  OR Schiff base formers >> Chemicals Activated by P450 to Glyoxal  >> Ethanolamines (including morpholine) OR SN1 OR SN1 >> Carbenium Ion Formation OR SN1 >> Carbenium Ion Formation >> Alpha halo ethers (including alpha halo thioethers) OR SN1 >> Carbenium Ion Formation >> Hydrazine OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Aromatic nitro OR SN1 >> Nitrenium Ion formation >> Aromatic phenylureas OR SN1 >> Nitrenium Ion formation >> Primary aromatic amine OR SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine OR SN2 OR SN2 >> P450 Mediated Epoxidation OR SN2 >> P450 Mediated Epoxidation >> Coumarins by DNA binding by OECD

Domain logical expression index: "i"

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: "j"

Referential boundary: The target chemical should be classified as Acylation >> Direct Acylation Involving a Leaving group >> Azlactone OR 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 >> alpha-Halocarbonyls OR SN2 >> SN2 reaction at sp3 carbon atom >> Thiophosphates OR SNAr OR SNAr >> Nucleophilic aromatic substitution OR SNAr >> Nucleophilic aromatic substitution >> Activated halo-benzenes by Protein binding by OECD

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Not possible to classify according to these rules (GSH) by Protein binding potency

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Highly reactive (GSH) OR Highly reactive (GSH) >> 3-Alken-2-ones (MA) OR Moderately reactive (GSH) OR Moderately reactive (GSH) >> 2-Chloroacetamides (SN2) OR Moderately reactive (GSH) >> 2-Vinyl carboxamides (MA) OR Moderately reactive (GSH) >> Substituted 1-Alken-3-ones (MA) by Protein binding potency

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as No superfragment by Superfragments ONLY

Domain logical expression index: "n"

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

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as No alert found by Protein binding alerts for Chromosomal aberration by OASIS v1.1

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as Ac-SN2 OR Ac-SN2 >> Acylation involving an activated (glucuronidated) carboxamide group OR Ac-SN2 >> Acylation involving an activated (glucuronidated) carboxamide group >> Carboxylic Acid Amines OR Ac-SN2 >> Direct acylation involving a leaving group OR Ac-SN2 >> Direct acylation involving a leaving group >> Carboxylic Acid Amines OR AN2 OR AN2 >> Michael-type addition to quinoid structures OR AN2 >> Michael-type addition to quinoid structures >> Carboxylic Acid Amines OR AN2 >> Michael-type addition to quinoid structures >> Phenols by Protein binding alerts for Chromosomal aberration by OASIS v1.1

Domain logical expression index: "q"

Parametric boundary:The target chemical should have a value of log Kow which is >= 0.0787

Domain logical expression index: "r"

Parametric boundary:The target chemical should have a value of log Kow which is <= 1.4

Validity criteria fulfilled:

not specified

Conclusions:

The short term toxicity on aquatic invertebrates was predicted for 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid (132-87-6). EC50 value was estimated to be 840.24 mg/l for Daphnia magna for 48 hrs duration. Based on this value it can be considered that the 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid (132-87-6) can be non-toxic to aquatic environment and can be considered as not classified as per the CLP classification criteria.

Executive summary:

Prediction based on the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the five closest read across substances, the short term toxicity on aquatic invertebrates was predicted for 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid (132-87-6). EC50 value was estimated to be 840.24 mg/l for Daphnia magna for 48 hrs duration. Based on this value it can be considered that the 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid (132-87-6) is likely to be non-toxic to aquatic environment and can be considered as not classified as per the CLP classification criteria.

Description of key information

Prediction based on the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the five closest read across substances, the short term toxicity on aquatic invertebrates was predicted for 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid (132-87-6). EC50 value was estimated to be 840.24 mg/l for Daphnia magna for 48 hrs duration. Based on this value it can be considered that the 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid (132-87-6) can be non-toxic to aquatic environment and can be considered as not classified as per the CLP classification criteria.

Key value for chemical safety assessment

Fresh water invertebrates

Fresh water invertebrates

Effect concentration:

840.24 mg/L

Additional information

Short term toxicity to aquatic invertebrates for 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid (132-87-6) was summaries with predicted data for target and by using functional read across studies as follows:

Prediction based on the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the five closest read across substances, the short term toxicity on aquatic invertebrates was predicted for 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid (132-87-6). EC50 value was estimated to be 840.24 mg/l for Daphnia magna for 48 hrs duration.

Another prediction done 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, the LC 50 value for short term toxicity to aquatic invertebrates was predicted. On the basis of this program, the LC 50 value for short term toxicity to aquatic invertebrates was predicted to be 5207.131mg/l for 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid in 48 hrs.

Read across study for acetylsalicylic acid (50-78-2) from Ecotoxicology and Environmental Safety 59 (2004) 309–315 was performed in Daphnia magna following the European Guideline (Commission of the European Communities,1992). Daphnids were bred in ADaM, a culture medium imitating natural freshwater. Test was performed in 20 degree C with photoperiods of 16 h light/8 h dark. Young daphnids were used in 50 ml of culture volume, each treatment was subdivided in four replicates, each containing 5 daphnia and observed for 24 and 48 hrs. After the experiment the EC 50 value for short term toxicity to aquatic invertebrates for Acetylsalicylic acid (50-78-2) was determined to be 88.1 mg/l. As the Acetylsalicylic acid was considered to toxic to aquatic invertebrates but it is readily biodegradable in nature hence, the Acetylsalicylic acid (50-78-2) was considered to be not classified as per the CLP regulations.

Study was performed in daphnia magna for read across Azepan-2-one (Caprolactam) from J-check, 2010 using OECD guideline 202. The test was performed for 48 hrs and EC 50 value was determined. After 48 hrs, the EC 50 value for Azepan-2-one (Caprolactam) for short term toxicity to aquatic invertebrates was determined to be >1000 mg/l.

From the same references of J-check, 2010, study of another read across was performed in daphnia magna using OECD guideline 202. The test was performed for 48 hrs and EC 50 value was determined. After 48 hrs, the EC 50 value for Acetic acid ethenyl ester was determined to be 9.2 mg/l.Based on the value, the Acetic acid ethenyl ester was considered to be toxic to aquatic invertebrates but as it was readily biodegradable in nature hence can be considered as not classified as per the CLP regulations.

Based on the all the weight of evidences, it was considered that 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid (132-87-6) was considered to be non-toxic to aquatic organism and can be considered to be not classified for toxicity to aquatic organism as per the CLP regulations.