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Environmental fate & pathways

Biodegradation in water and sediment: simulation tests

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Reference
Endpoint:
biodegradation in water: simulation testing on ultimate degradation in surface water
Type of information:
(Q)SAR
Adequacy of study:
key study
Study period:
January 2021
Reliability:
1 (reliable without restriction)
Rationale for reliability incl. deficiencies:
results derived from a valid (Q)SAR model and falling into its applicability domain, with adequate and reliable documentation / justification
Justification for type of information:
Given the final decision of ECHA (received on 31 January 2017) a simulation biodegradation study (EU C.25. / OECD 309: Aerobic Mineralisation in Surface Water – Simulation Biodegradation Test) typically carried out with 14C-labelled test substance must be performed. Given the complex, partly unknown and variable composition of Amine C8 (CAS 68909-77-3), accurate assessment and experimental testing of all individual UVCB components is challenging. In order to identify the relevant degradation products of Amine C8 (CAS 68909-77-3) as a standard information requirement according to Column 1, Section 9.2.3 of Annex IX to REACH and for assessment of potential PBT/vPvB properties, degradation products were predicted using the EAWAG-BBD Pathway Prediction System.

1. SOFTWARE
EAWAG-BBD Pathway Prediction System (http://eawag-bbd.ethz.ch/predict/)

2. MODEL (incl. version number)
EAWAG-BBD Pathway Prediction System: Last updated January 18, 2016.

3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL
See attached QPRF

4. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
The EAWAG-BBD Pathway Prediction System predicts (EAWAG-BBD PPS) microbial catabolic reactions using substructure searching, a rule-base, and atom-to-atom mapping. The system is able to recognize organic functional groups found in a compound and predict transformations based on biotransformation rules. The biotransformation rules are based on reactions found in the EAWAG-BBD database or in the scientific literature. The EAWAG-BBD database contains information on microbial biocatalytic reactions and biodegradation pathways for primarily xenobiotic, chemical compounds. Individual reactions and metabolic pathways are presented with information on the starting and intermediate chemical compounds, the organisms that transform the compounds, the enzymes, and the genes.
The EAWAG-BBD (Biocatalysis/Biodegradation Databaase) is a manually curated database containing information on over 1350 microbial catabolic reactions and about 200 biodegradation pathways. The EAWAG-PPS (Pathway Prediction System) predicts biodegradation pathways using 250 biotransformation rules based on data in the BBD (Biocatalysis/Biodegradation Database) and the scientific literature.
Further details can be found in the attached QMRF

5. APPLICABILITY DOMAIN
Athough there is no specifically identified applicability domain for EAWAG-BBD PPS, there are certain chemicals whose biodegradation profile should not be predicted with the system. There are a number of chemical classes that should not be investigated using the current version of the Pathway Prediction System (PPS). Compounds modeled with the EAWAG-BBD PPS can be structurally compared to the compounds present in the EAWAG-BBD database, which presently contains 1400 compounds. The experimental biotransformation data on which the biotransformation rules within the model are based, originate from data on these 1400 substances. More information on the models applicability domain can be found in the attached QMRF and QPRF.

6. ADEQUACY OF THE RESULT
The results are considered appropriate to fulfil the REACH requirements for identification of degradation products (Annex IX, Section 9.2.3.). The compounds meet the criteria for applicability of the EAWAG-BBD model. None of the constituents fall within the categories of chemicals that should not be investigated with the model. In addition, the (sub)structures of the compounds are well represented within the 1400 compounds in the EAWAG-BBD database.
More information on this can be found in the attached QPRF.
Reason / purpose for cross-reference:
other: Record containing QSAR data on acute toxicity to fish, used in the attached discussion document "AmineC8_Degradation_products.pdf" for the PBT assessment of biodegradation products.
Reason / purpose for cross-reference:
other: Record containing QSAR data on toxicity to algae, used in the attached discussion document "AmineC8_Degradation_products.pdf" for the PBT assessment of biodegradation products.
Reason / purpose for cross-reference:
other: Record containing QSAR data on acute toxicity to invertebrates, used in the attached discussion document "AmineC8_Degradation_products.pdf" for the PBT assessment of biodegradation products.
Reason / purpose for cross-reference:
other: Record containing QSAR data on BCF values for fish, used in the attached discussion document "AmineC8_Degradation_products.pdf" for the PBT assessment of biodegradation products.
Reason / purpose for cross-reference:
other: Record containing QSAR data on Log Kow, used in the attached discussion document "AmineC8_Degradation_products.pdf" for the PBT assessment of biodegradation products.
Reason / purpose for cross-reference:
other: Record containing QSAR data on ready biodegradation, used in the attached discussion document "AmineC8_Degradation_products.pdf" for the PBT assessment of biodegradation products.
Principles of method if other than guideline:
- Software tool(s) used including version: EAWAG-BBD (last update: January 2016)
- Model(s) used: EAWAG-BBD Pathway Prediction System
- Model description: see field 'Justification for non-standard information', see attached QMRF
- Justification of QSAR prediction: see field 'Justification for type of information', see attached QPRF
GLP compliance:
no
Specific details on test material used for the study:
SMILES codes for calculation: see attached QPRF.
Oxygen conditions:
aerobic
Inoculum or test system:
other: model calculation
Details on source and properties of surface water:
The model makes predictions for chemicals exposed to air, moist soil or water at moderate temperature and pH
Parameter followed for biodegradation estimation:
other: The model predicts formation of metabolites via known microbial biodegradation pathways, and provides a likelihood that this would occur under aerobic conditions.
Details on study design:
For the purpose of this QSAR analysis, only products formed through "Very likely" and "Likely" reactions were included.
Key result
Remarks on result:
other: formation of 42 transformation products via aerobic degradation was predicted; 11 transformation products were predicted to be not readily biodegradable, 31 were predicted to be readily biodegradable.
Transformation products:
not specified

The EAWAG-BBD PPS system predicted that the metabolites in the table below would be likely or very likely formed by aerobic microbial degradation. 





























































































































































































































Name



CAS number



Smiles



2-(2-aminoethoxy)acetaldehyde



NA



NCCOCC=O



2-(2-aminoethoxy)acetate 



NA



NCCOCC([O-])=O



2-(2-oxoethoxy)acetate 



NA



[O-]C(=O)COCC=O



diglycolate



110-99-6



[O-]C(=O)COCC([O-])=O



2-(2-hydroxyethoxy)acetaldehyde



NA



OCCOCC=O



2-Hydroxyethoxyacetate  



13382-47-3



OCCOCC([O-])=O



2-[2-(ethylamino)ethoxy]acetaldehyde



NA



CCNCCOCC=O



2-[2-(ethylamino)ethoxy]acetate



NA



CCNCCOCC([O-])=O



2-(morpholin-4-yl)acetaldehyde



NA



O=CCN1CCOCC1



2-(morpholin-4-yl)acetate



NA



[O-]C(=O)CN1CCOCC1



2-{[2-(2-oxoethoxy)ethyl]amino}acetate



NA



[O-]C(=O)CNCCOCC=O



2-{[2-(carboxylatomethoxy)ethyl]amino}acetate



NA



[O-]C(=O)COCCNCC([O-])=O



2-{2-[(2-aminoethyl)amino]ethoxy}acetaldehyde



NA



NCCNCCOCC=O



2-{2-[(2-aminoethyl)amino]ethoxy}acetate 



NA



NCCNCCOCC([O-])=O



2-{2-[(2-oxoethyl)amino]ethoxy}acetate



NA



[O-]C(=O)COCCNCC=O



2-[2-(morpholin-4-yl)ethoxy]acetaldehyde



NA



O=CCOCCN1CCOCC1



2-[2-(morpholin-4-yl)ethoxy]acetate



NA



[O-]C(=O)COCCN1CCOCC1



2-(2-{[2-(2-oxoethoxy)ethyl]amino}ethoxy)acetate



NA



[O-]C(=O)COCCNCCOCC=O



2-(2-{[2-(carboxylatomethoxy)ethyl]amino}ethoxy)acetate



NA



[O-]C(=O)COCCNCCOCC([O-])=O



2-(2-{[2-(2-hydroxyethoxy)ethyl]amino}ethoxy)acetaldehyde



NA



OCCOCCNCCOCC=O



2-(2-{[2-(2-hydroxyethoxy)ethyl]amino}ethoxy)acetate



NA



OCCOCCNCCOCC([O-])=O



2-(2-{[2-(2-aminoethoxy)ethyl]amino}ethoxy)acetaldehyde



NA



NCCOCCNCCOCC=O



2-(2-{[2-(2-aminoethoxy)ethyl]amino}ethoxy)acetate



NA



NCCOCCNCCOCC([O-])=O



2-(2-aminoethoxy)ethan-1-amine



NA



NCCOCCN



2-[2-({2-[2-(morpholin-4-yl)ethoxy]ethyl}amino)ethoxy]acetaldehyde



NA



O=CCOCCNCCOCCN1CCOCC1



2-[2-({2-[2-(morpholin-4-yl)ethoxy]ethyl}amino)ethoxy]acetate



NA



[O-]C(=O)COCCNCCOCCN1CCOCC1



17-(morpholin-4-yl)-3,9,15-trioxa-6,12-diazaheptadecanal



NA



O=CCOCCNCCOCCNCCOCCN1CCOCC1



17-(morpholin-4-yl)-3,9,15-trioxa-6,12-diazaheptadecanoate



NA



[O-]C(=O)COCCNCCOCCNCCOCCN1CCOCC1



2-[2-({2-[2-(morpholin-4-yl)ethoxy]ethyl}amino)ethoxy]ethan-1-ol



NA



OCCOCCNCCOCCN1CCOCC1



17-hydroxy-3,9,15-trioxa-6,12-diazaheptadecanal



NA



OCCOCCNCCOCCNCCOCC=O



17-hydroxy-3,9,15-trioxa-6,12-diazaheptadecanoate



NA



OCCOCCNCCOCCNCCOCC([O-])=O



17-oxo-3,9,15-trioxa-6,12-diazaheptadecanoate



NA



[O-]C(=O)COCCNCCOCCNCCOCC=O



3,9,15-trioxa-6,12-diazaheptadecanedioate



NA



[O-]C(=O)COCCNCCOCCNCCOCC([O-])=O



2-(2-{[2-(2-aminoethoxy)ethyl]amino}ethoxy)ethanol



NA



NCCOCCNCCOCCO



23-oxo-3,9,15,21-tetraoxa-6,12,18-triazatricosanoate



NA



[O-]C(=O)COCCNCCOCCNCCOCCNCCOCC=O



3,9,15,21-tetraoxa-6,12,18-triazatricosanedioate



NA



[O-]C(=O)COCCNCCOCCNCCOCCNCCOCC([O-])=O



17-amino-3,9,15-trioxa-6,12-diazaheptadecanoate 



NA



NCCOCCNCCOCCNCCOCC([O-])=O



bis[2-(2-aminoethoxy)ethyl]amine



NA



NCCOCCNCCOCCN



2-(2-{[2-(morpholin-4-yl)ethyl]amino}ethoxy)acetaldehyde



NA



O=CCOCCNCCN1CCOCC1



2-(2-{[2-(morpholin-4-yl)ethyl]amino}ethoxy)acetate



NA



[O-]C(=O)COCCNCCN1CCOCC1



14-oxo-3,12-dioxa-6,9-diazatetradecanoate



NA



[O-]C(=O)COCCNCCNCCOCC=O



3,12-dioxa-6,9-diazatetradecanedioate



NA



[O-]C(=O)COCCNCCNCCOCC([O-])=O



 

Conclusions:
Degradation (end) products of Amine C8 constituents were identified by use of QSAR.
The EAWAG-BBD Pathway Prediction System identified 42 metabolites for Amine C8 (CAS no. 68909-77-3) likely or very likely to be formed by microbial degradation under aerobic conditions.
Executive summary:

Given the final decision of ECHA (received on 31 January 2017) a simulation biodegradation study (EU C.25. / OECD 309: Aerobic Mineralisation in Surface Water – Simulation Biodegradation Test) typically carried out with 14C-labelled test substance must be performed. Given the complex, partly unknown and variable composition of Amine C8 (CAS 68909-77-3), accurate assessment and experimental testing of all individual UVCB components is challenging. In order to identify the relevant degradation products of Amine C8 (CAS 68909-77-3) as a standard information requirement according to Column 1, Section 9.2.3 of Annex IX to REACH and for assessment of potential PBT/vPvB properties, degradation products were predicted using the EAWAG-BBD Pathway Prediction System. The PBT/vPvB assessments of Amine C8 as well as the predicted (end) degradation products were determined and are included in report "AmineC8_Degradation_products.pdf". QMRF and QPRF documentation has been included to support the QSAR modeling results. 

Description of key information

A QSAR exercise was completed for the endpoint coverage. Given the complex, partly unknown and variable composition of the parent compound Amine C8 (CAS 68909-77-3), accurate assessment and experimental testing of all individual UVCB constituents is challenging. A QSAR exercise was performed aiming to identify the potential biodegradation pathway of each “representative” component of UVCB Amine C8 could follow. Once these potential pathways were constructed, the intermediates and end products were assessed for their P (B and T) properties in view of the PBT/vPvB assessment.

 

The relevant degradation products of Amine C8 were identified by means of the EAWAG-BBD Pathway Prediction System model. The biodegradability of each of these degradation products was predicted using the QSAR model BIOWIN available in the EPI Suite software. 42 degradation products were identified, of which 11 were predicted to be not readily biodegradable. The remaining 31 degradation products were predicted to be readily biodegradable. 

Key value for chemical safety assessment

Additional information