7-acetamido-4-hydroxynaphthalene-2-sulphonic acid

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:

according 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 (IUPAC name): 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid
- Molecular formula: C12H11NO5S
- Molecular weight: 281.2869 g/mol
- Smiles notation: CC(=O)Nc1ccc2c(c1)cc(cc2O)S(=O)(=O)O
- InChl: 1S/C12H11NO5S/c1-7(14)13-9-2-3-11-8(4-9)5-10(6-12(11)15)19(16,17)18/h2-6,15H,1H3,(H,13,14)(H,16,17,18)
- Substance type: Organic
- Physical state: Solid

Oxygen conditions:

aerobic

Inoculum or test system:

other: Microorganisms

Duration of test (contact time):

28 d

Based on:

not specified

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: BOD

Value:

0.571

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 0.57% 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 7 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 "n" )  )

Domain logical expression index: "a"

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

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 >> Quinoneimines 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 >> Amino Anthraquinones 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 >> 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) >> Coumarins OR Radical >> Radical mechanism via ROS formation (indirect) >> Fused-Ring Primary Aromatic Amines OR Radical >> Radical mechanism via ROS formation (indirect) >> Geminal Polyhaloalkane Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitro Azoarenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones OR Radical >> Radical mechanism via ROS formation (indirect) >> Single-Ring Substituted Primary Aromatic Amines OR Radical >> ROS formation after GSH depletion (indirect) OR Radical >> ROS formation after GSH depletion (indirect) >> Quinoneimines 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 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 >> Nitro Azoarenes 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 >> 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 by DNA binding by OASIS v.1.3

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 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 >> 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 amides OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated esters OR SN1 OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Aromatic azo OR SN1 >> Nitrenium Ion formation >> Aromatic nitro OR SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine by DNA binding by OECD

Domain logical expression index: "i"

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

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Non binder, impaired OH or NH2 group OR Non binder, MW>500 OR Non binder, non cyclic structure OR Non binder, without OH or NH2 group by Estrogen Receptor Binding

Domain logical expression index: "k"

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: "l"

Referential boundary: The target chemical should be classified as Esters OR Neutral Organics OR Phenols, Poly OR Salt by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "m"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 206 Da

Domain logical expression index: "n"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 327 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

The test chemical 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid (CAS no. 6334 -97 -0) is predicted using QSAR toolbox version 3.3 with logKow as the primary descriptor. Test substance undergoes 0.57% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid (CAS no. 6334 -97 -0) is predicted using QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 0.57% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid 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

Various predicted data for the target compound 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid (CAS No. 6334-97-0) and supporting weight of evidence studies 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 OECD QSAR toolbox version 3.3 with logKow as the primary descriptor, percentage biodegradability of test chemical 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid(CAS No. 6334-97-0) was estimated.Test substance undergoes 0.57% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid was estimated to be not readily biodegradable in water.

 

In another prediction using the Estimation Programs Interface Suite (EPI suite, 2017), the biodegradation potential of the test compound7-acetamido-4-hydroxynaphthalene-2-sulfonic acid(CAS No. 6334-97-0) in the presence of mixed populations of environmental microorganisms was estimated. The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI Linear Model, MITI Non-Linear Model and Anaerobic Model (called as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid is expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, HSDB, 2017 and EnviChem, 2014) for the read across chemical 2, 4, 4’ – Trichloro – 2’-hydroxy diphenyl ether (CAS no. 3380-34-5), biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 2, 4, 4’ – Trichloro – 2’-hydroxy diphenyl ether. The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)) under aerobic conditions. Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of substance2, 4, 4’ – Trichloro – 2’-hydroxy diphenyl etherwas determined to be 0 and 1% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, 2, 4, 4’ – Trichloro – 2’-hydroxy diphenyl ether is considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 2, 4 – Dibromophenol (CAS no. 615-58-7) (J-CHECK and HSDB, 2017). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)) under aerobic conditions. Concentration of inoculum i.e, 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 2, 4 – Dibromophenol was determined to be0 and 2% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation,2, 4 – Dibromophenol is considered to be not readily biodegradable in nature.

 

For the read across chemical (2-hydroxy-4-(octyloxy)phenyl)(phenyl)methanone (CAS no. 1843-05-6), biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across chemical (2-hydroxy-4-(octyloxy)phenyl)(phenyl)methanone (HSDB, 2017). The study was performed according to OECD Guideline 301 B (Ready Biodegradability: CO2 Evolution Test) under aerobic conditions. Non-adapted activated sludge was used as a test inoculum during the study. Initial test substance conc. used in the study were 10.7 and 20.2 mg/l, respectively. The percentage degradation of substance (2 -hydroxy-4 -(octyloxy)phenyl)(phenyl) methanone was determined to be 5 -6% by using CO2 evolution parameter after 28 days. Thus, based on percentage degradation, (2 -hydroxy-4 -(octyloxy)phenyl)(phenyl)methanone is considered to be not readily biodegradable in nature.

 

In a supporting weight of evidence study from authoritative database (SRC PhysProp Database, 2017) and secondary source (HPVIS, 2017) for the read across chemical 2,4-bis(1,1-dimethylethyl)phenol (CAS no. 96-76-4),biodegradation experiment was conducted using method "BOD test for insoluble substances" for 28 days for evaluating the percentage biodegradability of read across substance 2,4 -bis(1,1 -dimethylethyl)phenol under aerobic conditions. Non-adapted activated sludge was used as a test inoculum for the study. Initial test chemical concentration used for the study was 34.5 mg/l. The percentage degradation of substance 2,4 -bis(1,1 -dimethylethyl)phenol was determined to be 2% by BOD parameter in 28 days.  Thus, based on percentage degradation, 2,4 -bis(1,1 -dimethylethyl)phenol is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid(from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK, HSDB, EnviChem, SRC PhysProp Database and secondary source HPVIS), it can be concluded that the test substance 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid can be expected to be not readily biodegradable in nature.