2-(3-hydroxypropyl)-6-[(3-hydroxypropyl)amino]-1H-benz[de]isoquinoline-1,3(2H)-dione

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: 3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione
- Molecular formula: C18H20N2O4
- Molecular weight: 328.366 g/mol
- Smiles notation: c1ccc2C(=O)N(CCCO)C(=O)c3ccc(NCCCO)c1c23
- InChl: 1S/C18H20N2O4/c21-10-2-8-19-15-7-6-14-16-12(15)4-1-5-13(16)17(23)20(18(14)24)9-3-11-22/h1,4-7,19,21-22H,2-3,8-11H2
- Substance type: Organic

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:

1.333

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 1.33% 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 6 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Imides (Acute toxicity) by US-EPA New Chemical Categories

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as SN1 OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Secondary aromatic amine by DNA binding by OECD ONLY

Domain logical expression index: "c"

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 ONLY

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as days - weeks by Biodeg primary (Biowin 4) ONLY

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Biodegrades Fast by Biodeg probability (Biowin 1) ONLY

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 2) ONLY

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 5) ONLY

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 6) ONLY

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as weeks - months by Biodeg ultimate (Biowin 3) ONLY

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as 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 Non binder, non cyclic structure by Estrogen Receptor Binding

Domain logical expression index: "l"

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

Domain logical expression index: "m"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 162 Da

Domain logical expression index: "n"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 338 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

The test chemical 3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of 3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione (CAS no. 52821 -24 -6) is predicted using QSAR toolbox version 3.3 with logKow as the primary descriptor. Test substance undergoes 1.33% degradation by BOD in 28 days.Thus, based on percentage degradation, the test chemical 3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione (CAS no. 52821 -24 -6) is predicted using QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 1.33% degradation by BOD in 28 days.Thus, based on percentage degradation, the test chemical 3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione 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 3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione(CAS No. 52821-24-6) 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 3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione(CAS No. 52821-24-6) was estimated.Test substance undergoes 1.33% degradation by BOD in 28 days.Thus, based on percentage degradation, the test chemical 3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione 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 3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione(CAS No. 52821-24-6) 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  3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione 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 1,2-dimethoxybenzene (CAS no. 66-81-9), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 4 -[(2R)-2 -[(1S,3S,5S)-3,5 -dimethyl-2 -oxocyclohexyl]-2 -hydroxyethyl]piperidine-2,6 –dione. The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)). 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 substance 4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione was determined to be1, 0 and 2% by BOD, O2 consumption, TOC removal, test mat. analysis and HPLC parameter in 28 days. Thus, based on percentage degradation, 4 -[(2R)-2 -[(1S,3S,5S)-3,5 -dimethyl-2 -oxocyclohexyl]-2 -hydroxyethyl]piperidine -2,6 -dione 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 5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione (CAS no. 50-06-6) (J-CHECK and HSDB, 2017). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)). 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 substance 5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione was determined to be 0 and 1% by BOD, O2 consumption, test mat. analysis, HPLC and TOC removal parameter in 28 days. Thus, based on percentage degradation, 5 -ethyl-5 -phenyl-1,3 -diazinane-2,4,6 -trione is considered to be not readily biodegradable in nature.

 

For the another read across chemical1,3,5-triallyl-1,3,5-triazinane-2,4,6-trione (CAS no. 1025-15-6)fromauthoritative database (J-CHECK, 2107), biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 1,3,5-triallyl-1,3,5-triazinane-2,4,6-trione. 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 substance 1,3,5-triallyl-1,3,5-triazinane-2,4,6-trione was determined to be 3 and 1% by BOD, TOC removal and HPLC parameter in 28 days. Thus, based on percentage degradation,1,3,5-triallyl-1,3,5-triazinane-2,4,6-trione is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione(from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK, HSDB and EnviChem), it can be concluded that the test substance3-(3-hydroxypropyl)-8-[(3-hydroxypropyl)amino]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dionecan be expected to be not readily biodegradable in nature.