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Environmental fate & pathways

Biodegradation in water and sediment: simulation tests

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Endpoint:
biodegradation in water: simulation testing on ultimate degradation in surface water
Type of information:
(Q)SAR
Adequacy of study:
key study
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:
In order to identify the relevant degradation products of JeffCat DPA (CAS# 63469-23-8) 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 EAWAGBBD 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 Database) 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
Although 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 modelled 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 model's 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.
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 "JeffCat DPA_Degradation_products.pdf" for the PBT assessment of biodegradation products.
Reason / purpose for cross-reference:
other: Record containing QSAR data on acute toxicity to aquatic invertebrates, used in the attached discussion document "JeffCat DPA_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 "JeffCat DPA_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 "JeffCat DPA_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 "JeffCat DPA_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 "JeffCat DPA_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" react
ions were included.
Key result
Remarks on result:
other: formation of 41 transformation products via aerobic degradation was predicted; 14 transformation products were predicted to be not readily biodegradable, 27 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



NA



NA



CC(O)CN(CCC(=O))CC(C)O



NA



NA



CNCCCN(CC(C)O)CC(C)O



NA



NA



CC(O)CN(CCCN(C)C)CC(=O)(C)



1-{[3-(Dimethylamino)propyl]amino}-2-propanol



77463-83-3



CC(O)CNCCCN(C)C



2-Hydroxypropanal



3913-65-3



CC(O)C=O



Diisopropanolamine



000110-97-4



CC(O)CNCC(C)O



3-(Dimethylamino)propanal



70058-23-0



CN(C)CCC=O



NA



NA



CC(O)CN(CCC(=O)(O))CC(C)O



1,1'-[(3-Aminopropyl)imino]di(2-propanol)



77355-06-7



CC(O)CN(CCCN)CC(C)O



NA



NA



CNCCCN(CC(C)O)CC(=O)(C)



3-(Methylamino)propanal



79036-83-2



CNCCC=O



NA



NA



CNCCCNCC(C)O



1,1'-[(3-Hydroxypropyl)imino]diacetone



NA



CC(O)CN(CCC(=O))CC(=O)(C)



NA



NA



CN(C)CCCN(CC(=O)(C))CC(=O)(C)



1-{[3-(Dimethylamino)propyl]amino}acetone



NA



CN(C)CCCNCC(=O)(C)



1-[(2-Hydroxypropyl)amino]acetone



138169-32-1



CC(O)CNCC(=O)(C)



2-Oxopropanal (Methylglyoxal)



78-98-8



CC(=O)C=O



NA



NA



CC(O)CNCCC=O



3-(dimethylamino)-1-propylamine



203-680-9



CN(C)CCCN



1-amino-2-propanol



000078-96-6



CC(O)CN



Lactic acid



000050-21-5



CC(O)C(=O)(O)



3-dimethylaminopropionic acid



6300-04-5



CN(C)CCC(=O)(O)



2-Oxopropanoic acid



127-17-3



CC(=O)C(=O)(O)



NA



NA



CC(O)CNCCC(=O)(O)



3-Oxopropanoic acid



926-61-4



OC(=O)CC=O



NA



NA



CC(O)CN(CCC(=O)(O))CC(=O)(C)



NA



NA



CC(O)CN(CCCN)CC(=O)(C)



1-[(3-Aminopropyl)amino]-2-propanol



NA



CC(O)CNCCCN



3-Aminopropanal



352-92-1



NCCC=O



1-Amino-2-propanone



298-08-8



CC(=O)CN



NA



NA



CC(=O)CN(CCC(=O))CC(=O)(C)



1,1'-Iminodiacetone



133746-27-7



CC(=O)CNCC(=O)(C)



NA



NA



CC(=O)CNCCC=O



N-Methyl-β-alanin



2679-14-3



CNCCC(=O)(O)



NA



NA



CNCCCN(CC(=O)(C))CC(=O)(C)



NA



NA



CNCCCNCC(=O)(C)



(2Z)-3-(Methylamino)acrylonitrile                



74300-87-1



CNCCCN



NA



NA



CC(=O)CN(CCC(=O)(O))CC(=O)(C)



(2E)-3-[(2-Hydroxypropyl)amino]acrylic acid



NA



CC(=O)CNCCC(=O)(O)



NA



NA



CC(=O)CNCCCN



Methylamine



000074-89-5



CN


Conclusions:
Degradation (end) products of JeffCat DPA were identified by use of QSAR.
The EAWAG-BBD Pathway Prediction System identified 41 metabolites for JeffCat DPA (CAS# 63469-23-8) likely or very likely to be formed by microbial degradation under aerobic conditions.
Executive summary:

In order to identify the relevant degradation products of JeffCat DPA (CAS# 63469-23-8) 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 Jeffcat DPA 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 modelling results.

Endpoint:
biodegradation in water: sediment simulation testing
Data waiving:
exposure considerations
Justification for data waiving:
the study does not need to be conducted because direct and indirect exposure of sediment is unlikely

Description of key information

A QSAR exercise was completed for endpoint coverage. The relevant degradation products of the substance were identified by means of EAWAG-BBD Pathway Prediction System model. 41 degradation products were identified, and these were then assessed for their P (B and T) properties in view of the PBT/vPvB assessment.


The biodegradability of each of the degradation products was predicted using the QSAR model BIOWIN available in the EPI Suite software. Of the 41 degradation products, 14 were predicted to be not readily biodegradable. The remaining 27 degradation products were predicted to be readily biodegradable.


 

Key value for chemical safety assessment

Additional information