[4-[[4-anilino-1-naphthyl][4-(dimethylamino)phenyl]methylene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium acetate

Bioaccumulation: aquatic / sediment

Link to relevant study record(s)

Reference

Endpoint:

bioaccumulation in aquatic species: fish

Type of information:

calculation (if not (Q)SAR)

Adequacy of study:

weight of evidence

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Justification for type of information:

Estimated data generated using the EPI Suite program developed by the USEPA.

Qualifier:

according to guideline

Guideline:

other: Modelling database

Principles of method if other than guideline:

Prediction done using BCFBAF (v3.00) model

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material : N-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate- Molecular formula: C33H32N3C2H3O2- Molecular weight: 529.68 g/mol- Smiles notation : [N+](=C1/C=CC(\C=C1)=C(\c1ccc(c2ccccc12)Nc1ccccc1)c1ccc(cc1)N(C)C)(\C)C.C(C)(=O)[O-]- InChl : 1S/C33H31N3.C2H4O2/c1-35(2)27-18-14-24(15-19-27)33(25-16-20-28(21-17-25)36(3)4)31-22-23-32(30-13-9-8-12-29(30)31)34-26-10-6-5-7-11-26;1-2(3)4/h5-23H,1-4H3;1H3,(H,3,4)- Substance type: Organic- Physical state: Liquid

Radiolabelling:

not specified

Vehicle:

not specified

Test organisms (species):

other: Fish

Route of exposure:

aqueous

Test type:

not specified

Water / sediment media type:

natural water: freshwater

Test temperature:

25 deg.C

Reference substance (positive control):

not specified

Key result

Temp.:

25 °C

Type:

BCF

Value:

3.162 L/kg

Basis:

whole body w.w.

Calculation basis:

other: estimated

Remarks on result:

other: Non Bioaccumulative

BCFBAF Program (v3.01) Results:

==============================

SMILES : CC(=O)ON(C)(C)=C1C=CC(=C(c4ccc(N(C)C)cc4)c2ccc(Nc5ccccc5)c3ccccc23)C=

C1

CHEM :

MOL FOR: C35 H35 N3 O2

MOL WT : 529.69

--------------------------------- BCFBAF v3.01 --------------------------------

Summary Results:

Log BCF (regression-based estimate): 0.50 (BCF = 3.16 L/kg wet-wt)

Biotransformation Half-Life (days) : 9.12 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): 3.46 (BAF = 2.92e+003 L/kg wet-wt)

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 4.86

Equation Used to Make BCF estimate:

Log BCF = 0.50 (Ionic; Log Kow dependent)

Estimated Log BCF = 0.500 (BCF = 3.162 L/kg wet-wt)

Validity criteria fulfilled:

not specified

Conclusions:

The bioconcentration factor (BCF) of N-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical is not expected to bioaccumulate in the food chain.

Executive summary:

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical N-(4 -((4 -(dimethylamino)phenyl) (4 -(phenylamino)naphthalen-1 -yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (CAS No. 83803 -79 -6). The bioconcentration factor (BCF) of N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl) methylene)cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate is not expected to bioaccumulate in the food chain.

Description of key information

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical N-(4 -((4 -(dimethylamino)phenyl) (4 -(phenylamino)naphthalen-1 -yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (CAS No. 83803 -79 -6). The bioconcentration factor (BCF) of N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl) methylene)cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate is not expected to bioaccumulate in the food chain.

Key value for chemical safety assessment

BCF (aquatic species):

3.162 L/kg ww

Additional information

Various predicted data for the target compound N-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (CAS No. 83803-79-6) and supporting weight of evidence study for its read across substance were reviewed for the bioaccumulation end point which are summarized as below:

 

In aprediction done using theBCFBAF Program(v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical N-(4 -((4 -(dimethylamino)phenyl) (4 -(phenylamino)naphthalen-1 -yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (CAS No. 83803 -79 -6). The bioconcentration factor (BCF) of N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate was estimated to be 3.162 L/kg whole body w.w (at 25 deg C).

 

From CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application)  V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical), the bioaccumulation i.e BCF for test substance N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl)methylene)cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate was estimated to be 601 dimensionless . The predicted BCF result based on the 5 OECD principles.

 

In a supporting weight of evidence study from authoritative database (HSDB, 2017) for the read across chemical (4-(4,4'-Bis(dimethylamino)benzhydrylidene)cyclohexa-2,5-dien-1-ylidene)dimethylammonium, chloride (CAS no. 548-62-9),the bioaccumulation experiment in fish was conducted for estimating the BCF (bioaccumulation factor) value of read across chemical (4 -(4,4'-Bis(dimethylamino)benzhydrylidene)cyclohexa-2,5 -dien-1 -ylidene)dimethylammonium, chloride. The bioaccumulation factor (BCF) value was calculated using a log Kow of 0.51 and a regression-derived equation. The estimated BCF (bioaccumulation factor) valueof(4-(4,4'-Bis(dimethylamino)benzhydrylidene)cyclohexa-2,5-dien-1-ylidene)dimethylammonium, chloride was determined to be 3 dimensionless.

 

For the read across chemical 4-[(4-dimethylaminophenyl)-phenylmethylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium chloride (CAS no. 569-64-2),bioaccumulation study in fish was conducted for estimating the BCF (bioaccumulation factor) value of read across chemical 4 -[(4 -dimethylaminophenyl)-phenylmethylidene] cyclohexa-2,5 -dien-1 -ylidene]-dimethylazanium chloride (HSDB, 2017). The bioaccumulation factor (BCF) value was calculated using a log Kow of 0.62 and a regression-derived equation. The estimated BCF (bioaccumulation factor) valueof 4-[(4-dimethylaminophenyl)-phenylmethylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium chloride was determined to be 3 dimensionless.

 

On the basis of above results for target chemicalN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate(from EPI suiteand CompTox Chemistry Dashboard,  2017) and for its read across substance (from authoritative database HSDB, 2017), it can be concluded that the BCF value of test substanceN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetateranges from 3.162 –601which does not exceed the bioconcentration threshold of 2000, indicating that the chemicalN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetateis not expected to bioaccumulate in the food chain.