Hydrogen [4-[4-(dimethylamino)-α-(2-hydroxy-3,6-disulphonato-1-naphthyl)benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium, monosodium salt

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Endpoint:

biodegradation in water: screening tests

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:

equivalent or similar to guideline

Guideline:

OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I))

Principles of method if other than guideline:

The data is predicted using the OECD QSAR toolbox version 3.3 with logKow as the primary descriptor.

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material (as cited in study report): Hydrogen [4-[4-(dimethylamino)-α-(2-hydroxy-3,6-disulphonato-1-naphthyl)benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium, monosodium salt
- Molecular formula (if other than submission substance): C27H26N2O7S2.Na
- Molecular weight (if other than submission substance): 576.623 g/mol
- Smiles notation (if other than submission substance): 1S/C27H26N2O7S2.Na/c1-28(2)20-9-5-17(6-10-20)25(18-7-11-21(12-8-18)29(3)4)26-23-14-13-22(37(31,32)33)15-19(23)16-24(27(26)30)38(34,35)36;/h5-16H,1-4H3,(H2,31,32,33,34,35,36);/q;+1/p-1
-InChI: c12c(\C(c3ccc(N(C)C)cc3)=C3/C=C\C(=[N+](/C)C)C=C3)c(O)c(S(=O)(=O)[O-])cc1cc(S(=O)(=O)[O-])cc2.[Na+]
- Substance type: Organic

Oxygen conditions:

aerobic

Inoculum or test system:

other: Microorganisms

Duration of test (contact time):

28 d

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: BOD

Value:

1.86

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 1.86% degradation by BOD in 28 days.

The prediction was based on dataset comprised from the following descriptors: BOD
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" or "g" )  and ("h" and ( not "i") )  )  and ("j" and ( not "k") )  )  and ("l" and ( not "m") )  )  and ("n" and "o" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Alkene AND Ammonium salt AND Aromatic amine AND Aryl AND Fused carbocyclic aromatic AND Naphtalene AND Phenol AND Sulfonic acid by Organic Functional groups

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Alkene AND Ammonium salt AND Aromatic amine AND Aryl AND Fused carbocyclic aromatic AND Naphtalene AND Overlapping groups AND Phenol AND Sulfonic acid by Organic Functional groups (nested)

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Alcohol, olefinic attach [-OH] AND Aliphatic Carbon [CH] AND Aliphatic Carbon [-CH2-] AND Aliphatic Carbon [-CH3] AND Aliphatic Nitrogen, one aromatic attach [-N] AND Amino, aliphatic attach [-N<] AND Aromatic Carbon [C] AND Hydroxy, aromatic attach [-OH] AND Miscellaneous sulfide (=S) or oxide (=O) AND Olefinic carbon [=CH- or =C<] AND Oxygen, one aromatic attach [-O-] AND Suflur {v+4} or {v+6} AND Sulfonate, aromatic attach [-SO2-O] by Organic functional groups (US EPA)

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Amine AND Anion AND Aromatic compound AND Cation AND Hydroxy compound AND Phenol AND Sulfonic acid derivative AND Tertiary amine AND Tertiary mixed amine by Organic functional groups, Norbert Haider (checkmol)

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Amine AND Anion AND Aromatic compound AND Cation AND Hydroxy compound AND Phenol AND Sulfonic acid derivative AND Tertiary amine AND Tertiary mixed amine 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 >> Tertiary aromatic amine by DNA binding by OECD

Domain logical expression index: "g"

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

Domain logical expression index: "h"

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

Domain logical expression index: "i"

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 >> Shiff base formation after aldehyde release OR AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters 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 >> Fused-Ring Primary Aromatic Amines OR Non-covalent interaction >> DNA intercalation >> Quinones OR Radical 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 via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Amino Anthraquinones OR Radical >> Radical mechanism via ROS formation (indirect) >> C-Nitroso Compounds OR Radical >> Radical mechanism via ROS formation (indirect) >> Fused-Ring Primary Aromatic Amines OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitro Azoarenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones OR SN1 OR SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> Specific Acetate Esters 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 >> Fused-Ring Primary Aromatic Amines OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitro Azoarenes OR SN1 >> Nucleophilic substitution after glutathione-induced nitrenium ion formation OR SN1 >> Nucleophilic substitution after glutathione-induced nitrenium ion formation >> C-Nitroso Compounds OR SN2 OR SN2 >> Acylation OR SN2 >> Acylation >> Specific Acetate Esters OR SN2 >> Alkylation, direct acting epoxides and related OR SN2 >> Alkylation, direct acting epoxides and related >> Epoxides and Aziridines 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 by DNA binding by OASIS v.1.3

Domain logical expression index: "j"

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

Domain logical expression index: "k"

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 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 No alert found 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 phenylureas by DNA binding by OECD

Domain logical expression index: "l"

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

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Non binder, without OH or NH2 group OR Strong binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "n"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 516 Da

Domain logical expression index: "o"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 793 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

The test chemical Hydrogen [4-[4-(dimethylamino)-α-(2-hydroxy-3,6-disulphonato-1-naphthyl)benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium, monosodium salt was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of Hydrogen [4-[4-(dimethylamino)-α-(2 -hydroxy-3,6 -disulphonato-1 -naphthyl)benzylidene]cyclohexa-2,5 -dien-1 -ylidene]dimethylammonium, monosodium salt (CAS no. 3087 -16 -9) is predicted using QSAR toolbox version 3.3 with logKow as the primary descriptor. Test substance undergoes 1.86% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical Hydrogen [4 -[4 -(dimethylamino)-α-(2 -hydroxy-3,6 -disulphonato-1 -naphthyl)benzylidene]cyclohexa-2,5 -dien-1 -ylidene]dimethylammonium, monosodium salt was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of Hydrogen [4-[4-(dimethylamino)-α-(2 -hydroxy-3,6 -disulphonato-1 -naphthyl)benzylidene]cyclohexa-2,5 -dien-1 -ylidene]dimethylammonium, monosodium salt (CAS no. 3087 -16 -9) is predicted using QSAR toolbox version 3.3 with logKow as the primary descriptor (2017). Test substance undergoes 1.86% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical Hydrogen [4 -[4 -(dimethylamino)-α-(2 -hydroxy-3,6 -disulphonato-1 -naphthyl)benzylidene]cyclohexa-2,5 -dien-1 -ylidene]dimethylammonium, monosodium salt was estimated to be not readily biodegradable in water.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

1 predicted data for the target compound Hydrogen [4-[4-(dimethylamino)-α-(2-hydroxy-3,6-disulphonato-1-naphthyl)benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium, monosodium salt(CAS no. 3087-16-9) and the total 3 weight of evidence studies (from authoritative database) for its closest read across substance with logKow as the primary descriptor were reviewed for the biodegradation end point which are summarized as below:

 

In a prediction done by SSS (2017) using QSAR toolbox version 3.3 with logKow as the primary descriptor, percentage biodegradability of test chemical Hydrogen [4-[4-(dimethylamino)-α-(2-hydroxy-3,6-disulphonato-1-naphthyl)benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium, monosodium salt(CAS no. 3087-16-9) was estimated. Test substance undergoes 1.86% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical Hydrogen [4 -[4 -(dimethylamino)-α-(2 -hydroxy-3,6 -disulphonato-1 -naphthyl)benzylidene]cyclohexa-2,5 -dien-1 -ylidene]dimethylammonium, monosodium salt was estimated to be not readily biodegradable in water.

 

In a weight of evidence study from authoritative database (J-CHECK, 2016) for read across substance sodium 3 -({[4 -([4 -(dimethylamino)phenyl]{4 -[ethyl(3 -sulfonatobenzyl)amino]phenyl}methylene)cyclohexa-2,5 -dien-1 -ylidene](ethyl)ammonio}methyl)benzenesulfonate(CAS no. 1694-09-3),biodegradation experiment was conducted for 28 days. Concentration of inoculum i.e, activated sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of read across substance was determined to be 1, 4 and 0% by BOD, TOC removal and HPLC parameter in 28 days. Thus, based on percentage degradation, sodium 3 -({[4 -([4 -(dimethylamino)phenyl]{4 -[ethyl(3 -sulfonatobenzyl)amino]phenyl}methylene)cyclohexa-2,5 -dien-1 -ylidene](ethyl)ammonio}methyl)benzenesulfonate is considered to be not readily biodegradable in nature.

 

Another supporting study of biodegradation was conducted for 28 days for evaluating the percentage biodegradability of read across substance sodium 4 -[3,6 -bis(diethylamino)-2,7 -dimethylxanthenium-9 -yl]benzene-1,3 -disulfonate (CAS no. 3520 -42 -1) (J-CHECK). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I) and other guideline “Biodegradation test of a chemical substance using a microorganism etc.” provided in “the Notice on the Test Method Concerning New Chemical Substances", respectively. Concentration of inoculum i.e, activated sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of read across substance was determined to be 6, 0 and 0% by O2 consumption, TOC removal, Test mat. analysis and HPLC parameter in 28 days. Thus, based on percentage degradation, sodium 4 -[3,6 -bis(diethylamino)-2,7 -dimethylxanthenium-9 -yl]benzene-1,3 -disulfonate is considered to be not readily biodegradable in nature.

 

In an additional study of read across substance 2'-anilino-6'-[cyclohexyl(methyl)amino]-3'-methyl-3H-spiro[2 -benzofuran-1,9'-xanthen]-3 -one (CAS no. 55250 -84 -5) from authoritative database (J-CHECK, 2016),concentration of inoculum i.e, activated sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of test substance was determined to be 0% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, 2'-anilino-6'-[cyclohexyl(methyl)amino]-3'-methyl-3H-spiro[2 -benzofuran-1,9'-xanthen]-3 -one is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemicalHydrogen [4-[4-(dimethylamino)-α-(2-hydroxy-3,6-disulphonato-1-naphthyl)benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium, monosodium salt(from OECD QSAR toolbox version 3.3) and for its read across substance (from authoritative database J-CHECK), it can be concluded that the test substance 4Hydrogen [4-[4-(dimethylamino)-α-(2-hydroxy-3,6-disulphonato-1-naphthyl)benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium, monosodium salt can be expected to be not readily biodegradable in nature.