7-benzamido-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:

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: 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

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:

2.45

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 2.45% 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" )  and "g" )  and ("h" and ( not "i") )  )  and ("j" and ( not "k") )  )  and "l" )  and ("m" and ( not "n") )  )  and ("o" and "p" )  )

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 days - weeks by Biodeg primary (Biowin 4) ONLY

Domain logical expression index: "h"

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

Domain logical expression index: "i"

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 >> 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 >> Primary aromatic amine OR SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine OR SN1 >> Nitrenium Ion formation >> Unsaturated heterocyclic azo OR SN2 OR SN2 >> P450 Mediated Epoxidation OR SN2 >> P450 Mediated Epoxidation >> Coumarins by DNA binding by OECD

Domain logical expression index: "j"

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

Domain logical expression index: "k"

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 OR Strong binder, NH2 group by Estrogen Receptor Binding

Domain logical expression index: "l"

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

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Aryl AND Benzamide AND Fused carbocyclic aromatic AND Naphtalene AND Phenol AND Sulfonic acid by Organic Functional groups

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Aniline OR Anthracenone/ Antracendione OR Aryl halide OR Carboxylic acid ester OR Cycloketone OR Diketone OR Ether OR Isopropyl OR Ketone by Organic Functional groups

Domain logical expression index: "o"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 246 Da

Domain logical expression index: "p"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 379 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

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

Executive summary:

Biodegradability of 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid (CAS no. 132 -87 -6) is predicted using OECD QSAR toolbox version 3.3. Test substance undergoes 2.45% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 7-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid (CAS no. 132 -87 -6) is predicted using OECD QSAR toolbox version 3.3 (2017). Test substance undergoes 2.45% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 7-(benzoylamino)-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-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid(CAS No. 132-87-6) 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 -(benzoyl amino)-4 -hydroxynaphthalene-2 -sulfonic acid(CAS No. 132-87-6) was estimated. Test substance undergoes 2.45% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 7-(benzoylamino)-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 compound 7 -(benzoylamino)-4 -hydroxy naphthalene-2 -sulfonic acid (CAS No. 132 -87 -6) 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-(benzoylamino)-4-hydroxynaphthalene-2-sulfonic acid is expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017 and EnviChem, 2014) for the read across chemical 3-hydroxy-2-naphthanilide (CAS no. 92-77-3), biodegradation experiment was conducted for 14 days for evaluating the percentage biodegradability of read across substance 3-hydroxy-2-naphthanilide. 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 was determined to be 5.4% by BOD parameter in 14 days. Thus, based on percentage degradation, 3 -hydroxy-2 -naphthanilide is considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 14 days for evaluating the percentage biodegradability of read across substance disodium 3 -hydroxynaphthalene-2,7 -disulfonate (CAS no. 135 -51 -3)(J-CHECK, 2017 and EnviChem, 2014). 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 was determined to be 4.4, 5.9 and 4.5% by BOD, TOC removal and UV-Vis parameter in 14 days. Thus, based on percentage degradation, disodium 3 -hydroxynaphthalene-2,7 -disulfonate is considered to be not readily biodegradable in nature.

 

For the read across chemical sodium 4-hydroxynaphthalene-1-sulfonate (CAS no. 6099-57-6), biodegradation study was conducted for 14 days for evaluating the percentage biodegradability of read across substance sodium 4 -hydroxynaphthalene-1 -sulfonate (CAS no. 6099 -57 -6) (J-CHECK, 2017). 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 was determined to be 0, 2.1 and 1% by BOD, TOC removal and UV-Vis parameter in 14 days. Thus, based on percentage degradation, sodium 4 -hydroxynaphthalene-1 -sulfonate is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical7-(benzoylamino)-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 and EnviChem, 2014), it can be concluded that the test substance 7 -(benzoylamino)-4 -hydroxynaphthalene-2 -sulfonic acid can be expected to be not readily biodegradable in nature.