(5or8)-aminonaphthalene-2-sulphonic acid

Endpoint summary

Key value for chemical safety assessment

Genetic toxicity in vitro

Description of key information

The test compound (5-Or8)aminonaphthalene-2-sulphonic acid is not likely to be a gene mutant in vitro.

Link to relevant study records

Reference

Endpoint:

in vitro gene mutation study in mammalian cells

Type of information:

(Q)SAR

Adequacy of study:

weight of evidence

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Data is from prediction database

Justification for type of information:

Data is from prediction database

Qualifier:

according to guideline

Guideline:

other: Prediction is done using QSAR Toolbox version 3.3

Principles of method if other than guideline:

Prediction is done using QSAR Toolbox version 3.3

GLP compliance:

no

Specific details on test material used for the study:

- Name of test material: (5-Or8)aminonaphthalene-2-sulphonic acid
- Molecular formula: C10H9NO3S
- Molecular weight: 223.2511 g/mol
- Smiles notation: c1cc2cc(ccc2c(c1)N)S(=O)(=O)O
- Substance type: Organic

Species / strain / cell type:

S. typhimurium TA 100

Details on mammalian cell type (if applicable):

no data

Additional strain / cell type characteristics:

not specified

Metabolic activation:

with

Metabolic activation system:

S9 activation system

Test concentrations with justification for top dose:

No data

Vehicle / solvent:

No data

Untreated negative controls:

not specified

Negative solvent / vehicle controls:

not specified

True negative controls:

not specified

Positive controls:

not specified

Positive control substance:

not specified

Remarks:

not specified

Details on test system and experimental conditions:

No data

Rationale for test conditions:

No data

Evaluation criteria:

No data

Statistics:

No data

Species / strain:

S. typhimurium TA 100

Metabolic activation:

with

Genotoxicity:

negative

Cytotoxicity / choice of top concentrations:

not specified

Vehicle controls validity:

not specified

Untreated negative controls validity:

not specified

Positive controls validity:

not specified

The prediction was based on dataset comprised from the following descriptors: "Gene mutation"
Estimation method: Takes highest mode value from the 5 nearest neighbours
Domain  logical expression:Result: In Domain

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

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 Aniline AND Aryl AND Fused carbocyclic aromatic AND Naphtalene AND Sulfonic acid by Organic Functional groups

Domain logical expression index: "c"

Referential boundary:The target chemical should be classified as Aniline AND Fused carbocyclic aromatic AND Naphtalene AND Overlapping groups AND Sulfonic acid by Organic Functional groups (nested)

Domain logical expression index: "d"

Referential boundary:The target chemical should be classified as Aliphatic Nitrogen, one aromatic attach [-N] AND Aromatic Carbon [C] AND Hydroxy, sulfur attach [-OH] AND Miscellaneous sulfide (=S) or oxide (=O) AND Olefinic carbon [=CH- or =C<] AND Suflur {v+4} or {v+6} AND Sulfinic acid [-S(=O)OH] AND Sulfonate, aromatic attach [-SO2-O] by Organic functional groups (US EPA)

Domain logical expression index: "e"

Referential boundary:The target chemical should be classified as Amine AND Aromatic compound AND Primary amine AND Primary aromatic amine AND Sulfonic acid AND Sulfonic acid derivative by Organic functional groups, Norbert Haider (checkmol)

Domain logical expression index: "f"

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: "g"

Referential boundary:The target chemical should be classified as 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 >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Polycyclic (PAHs) and heterocyclic (HACs) aromatic hydrocarbons-Michael addition OR Michael addition >> Polarised Alkenes-Michael addition OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated ketones OR Michael addition >> Quinones and Quinone-type Chemicals OR Michael addition >> Quinones and Quinone-type Chemicals >> Quinones OR No alert found OR SN1 >> Carbenium Ion Formation OR SN1 >> Carbenium Ion Formation >> Hydrazine OR SN1 >> Carbenium Ion Formation >> Polycyclic (PAHs) and heterocyclic (HACs) aromatic hydrocarbons-SN1 OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines OR SN1 >> Nitrenium Ion formation >> Aromatic azo OR SN1 >> Nitrenium Ion formation >> Aromatic nitro OR SN1 >> Nitrenium Ion formation >> Aromatic phenylureas OR SN1 >> Nitrenium Ion formation >> Secondary aromatic amine OR SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine OR SN1 >> Nitrenium Ion formation >> Unsaturated heterocyclic azo by DNA binding by OECD

Domain logical expression index: "h"

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

Domain logical expression index: "i"

Referential boundary:The target chemical should be classified as Moderate binder, NH2 group OR Moderate binder, OH grooup OR Non binder, MW>500 OR Strong binder, OH group OR Weak binder, NH2 group OR Weak binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "j"

Referential boundary:The target chemical should be classified as AN2 AND AN2 >> Michael-type addition to quinoid structures  AND AN2 >> Michael-type addition to quinoid structures  >> Substituted Anilines by Protein binding by OASIS v1.4

Domain logical expression index: "k"

Referential boundary:The target chemical should be classified as Acylation OR Acylation >> Acylation involving an activated (glucuronidated) carboxamide group OR Acylation >> Acylation involving an activated (glucuronidated) carboxamide group >> Carboxylic Acid Amides OR Acylation >> Acylation involving an activated (glucuronidated) ester group OR Acylation >> Acylation involving an activated (glucuronidated) ester group >> Arenecarboxylic Acid Esters OR Acylation >> Acylation involving an activated (glucuronidated) sulfonamide group OR Acylation >> Acylation involving an activated (glucuronidated) sulfonamide group >> Arenesulfonamides OR Acylation >> Direct acylation involving a leaving group OR Acylation >> Direct acylation involving a leaving group >> Carboxylic Acid Amides OR Acylation >> Direct acylation involving a leaving group >> N-Carbonylsulfonamides OR Acylation >> Ester aminolysis OR Acylation >> Ester aminolysis >> Amides OR AN2 >> Michael addition to activated double bonds OR AN2 >> Michael addition to activated double bonds >> alpha,beta-Unsaturated Carbonyls and Related Compounds OR AN2 >> Michael-type addition to quinoid structures  >> Carboxylic Acid Amides OR AN2 >> Michael-type addition to quinoid structures  >> N-Substituted Aromatic Amines OR AN2 >> Nucleophilic addition at polarized N-functional double bond OR AN2 >> Nucleophilic addition at polarized N-functional double bond >> Arenesulfonamides OR AN2 >> Nucleophilic addition to pyridonimine tautomer of aminopyridoindoles or aminopyridoimidazoles (hypothesized) OR AN2 >> Nucleophilic addition to pyridonimine tautomer of aminopyridoindoles or aminopyridoimidazoles (hypothesized) >> Heterocyclic Aromatic Amines OR Michael addition OR Michael addition >> Michael addition on conjugated systems with electron withdrawing group OR Michael addition >> Michael addition on conjugated systems with electron withdrawing group >> Activated electrophilic ethenylarenes  OR Radical reactions OR Radical reactions >> ROS generation and direct attack of hydroxyl radical to the C8 position of nucleoside base OR Radical reactions >> ROS generation and direct attack of hydroxyl radical to the C8 position of nucleoside base >> Heterocyclic Aromatic Amines OR SE reaction (CYP450-activated heterocyclic amines) OR SE reaction (CYP450-activated heterocyclic amines) >> Direct attack of arylnitrenium cation to the C8 position of nucleoside base  OR SE reaction (CYP450-activated heterocyclic amines) >> Direct attack of arylnitrenium cation to the C8 position of nucleoside base  >> Heterocyclic Aromatic Amines OR SN2 OR SN2 >> Nucleophilic substitution at sp3 carbon atom OR SN2 >> Nucleophilic substitution at sp3 carbon atom >> (Thio)Phosphates  OR SN2 >> SN2 Reaction at a sp3 carbon atom OR SN2 >> SN2 Reaction at a sp3 carbon atom >> Activated alkyl esters and thioesters  OR SR reaction (peroxidase-activated heterocyclic amines) OR SR reaction (peroxidase-activated heterocyclic amines) >> Direct attack of arylnitrenium radical to the C8 position of nucleoside base OR SR reaction (peroxidase-activated heterocyclic amines) >> Direct attack of arylnitrenium radical to the C8 position of nucleoside base >> Heterocyclic Aromatic Amines by Protein binding by OASIS v1.4

Domain logical expression index: "l"

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

Domain logical expression index: "m"

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 >> Acetates by Protein binding by OECD

Domain logical expression index: "n"

Referential boundary:The target chemical should be classified as No alert found by Protein binding alerts for Chromosomal aberration by OASIS v.1.2

Domain logical expression index: "o"

Referential boundary:The target chemical should be classified as AN2 OR AN2 >> Michael addition to the quinoid type structures OR AN2 >> Michael addition to the quinoid type structures >> Substituted Anilines by Protein binding alerts for Chromosomal aberration by OASIS v.1.2

Domain logical expression index: "p"

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

Domain logical expression index: "q"

Similarity boundary:Target: Nc1cccc2cc(S(O)(=O)=O)ccc12
Threshold=40%,
Dice(Atom centered fragments)
Atom type; Count H attached; Hybridization

Domain logical expression index: "r"

Parametric boundary:The target chemical should have a value of log Kow which is >= -2.69

Domain logical expression index: "s"

Parametric boundary:The target chemical should have a value of log Kow which is <= 0.773

Conclusions:

The test compound (5-Or8)aminonaphthalene-2-sulphonic acid failed to induce mutation in Salmonella typihimurium strain TA100 with S9 activation system and hence is not likely to be a mutagenic in vitro.

Executive summary:

Gene mutation was predicted for the test chemical (5-Or8)aminonaphthalene-2-sulphonic acid using SSS QSAR prediction databse, 2016. The test assumed the use of Salmonella typihimurium strain TA100 with S9 activation system. The test compound (5-Or8)aminonaphthalene-2-sulphonic acid failed to induce mutation in Salmonella typihimurium strain TA100 with S9 activation system and hence is not likely to be a mutagenic in vitro.

Endpoint conclusion

Endpoint conclusion:

no adverse effect observed (negative)

Additional information

Additional information from genetic toxicity in vitro:

Gene mutation in vitro:

Prediction model based estimation and data from read across have been summarized to determine the mutagenic nature of the test compound (5-Or8)aminonaphthalene-2-sulphonic acid (CAS no 51548 -48 -2):

Gene mutation was predicted for the test chemical (5-Or8)aminonaphthalene-2-sulphonic acid (CAS no 51548 -48 -2) using SSS QSAR prediction databse, 2016. The test assumed the use of Salmonella typihimurium strain TA100 with S9 activation system. The test compound (5-Or8)aminonaphthalene-2-sulphonic acid failed to induce mutation in Salmonella typihimurium strain TA100 with S9 activation system and hence is not likely to be a mutagenic in vitro.

Gene mutation was predicted for the test chemical (5-Or8)aminonaphthalene-2-sulphonic acid (CAS no 51548 -48 -2) using SSS QSAR prediction databse, 2016. The test assumed the use of Salmonella typihimurium strain TA102 with S9 activation system. The test compound (5-Or8)aminonaphthalene-2-sulphonic acid failed to induce mutation in Salmonella typihimurium strain TA102 with S9 activation system and hence is not likely to be a mutagenic in vitro.

Gene mutation was predicted for the test chemical (5-Or8)aminonaphthalene-2-sulphonic acid (CAS no 51548 -48 -2) using SSS QSAR prediction databse, 2016. The test assumed the use of Salmonella typihimurium strain TA1535 without S9 activation system. The test compound (5-Or8)aminonaphthalene-2-sulphonic acid failed to induce mutation in Salmonella typihimurium strain TA1535 without S9 activation system and hence is not likely to be a mutagenic in vitro.

Gene mutation toxicity study was performed by Chung et al (1981) to evaluate the mutagenic response for the test chemical sodium 4-aminonaphthalene-1-sulphonate (RA CAS no 130 -13 -2). The study was performed using Salmonella typhimurium strains TA1537, TA1538, TA98,or TA100 with and without S9 metabolic activation system at dose levels of 5, 10, 25, 50, 100, 250, 500, 1000, 2500, 5000 µg.

Maximum nontoxic dose of test substance sodium 4-aminonaphthalene-1-sulphonate was tested that was nonmutagenic TA1537, TA1538, TA98,or TA100 with and without male rat Aroclor S9 mix. Thus, the test compound is not likely to be gene mutant in vitro.

Ames assay of genetic toxicity study was perfomed by Jung et al (1992) using Salmonella typhimurium being treated with 2-aminonaphthalene-6-sulphonic acid (RA CAS no 93 -00 -5).The test was performed in the presence of Aroclor-induced rat liver microsomalS-9cell fraction to observe the mutagenic effect of 6-aminonaphthalene-2-sulphonic acid. Non-mutagenic effects were found with S 9 metabollic activation toSalmonella typhimurium when treated with 6-aminonaphthalene-2-sulphonic acid. Hence is the test chemical is not likely to be a gene mutant in vitro.

Based on the weight of evidence data summarized, the test chemical (5-Or8)aminonaphthalene-2-sulphonic acid is not likely to be a gene mutant in vitro.

Justification for selection of genetic toxicity endpoint
Data is from prediction database

Justification for classification or non-classification

Based on the weight of evidence data summarized, the test chemical (5-Or8)aminonaphthalene-2-sulphonic acid is not likely to be a gene mutant in vitro.