Bis(p-aminophenyl)-4-methylenecyclohexa-2,5-dienylideneammonium acetate

Bioaccumulation: aquatic / sediment

Link to relevant study record(s)

Reference

Endpoint:

bioaccumulation in aquatic species, other

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: Modeling database

Principles of method if other than guideline:

Prediction done using BCFBAF (v3.01) model

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material (IUPAC name): Bis(p-aminophenyl)-4-methylenecyclohexa-2,5-dienylideneammonium acetate
- Common name: Bis(p-aminophenyl)-4-methylenecyclohexa-2,5-dienylideneammonium acetate
- Molecular formula: C21H21N3O2
- Molecular weight: 347.416 g/mol
- Smiles notation: N=C1C=C\C(C=C1)=C(\c1ccc(N)cc1)c1ccc(N)cc1.C(C)(=O)O
- InChl: 1S/C19H17N3.C2H4O2/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15;1-2(3)4/h1-12,20H,21-22H2;1H3,(H,3,4)
- Substance type: Organic
-Physical state: solid

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

Basis:

whole body w.w.

Calculation basis:

other: estimated

Remarks on result:

other: Non-bioaccumulative

BCFBAF Program (v3.01) Results:

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

SMILES : N=C(C=CC(C=1)=C(c(ccc(N)c2)c2)c(ccc(N)c3)c3)C1

CHEM : Benzenamine, 4-[(4-aminophenyl)(4-imino-2,5-cyclohexadien-1-ylidene)m

ethyl]-, monoacetate

MOL FOR: C19 H17 N3

MOL WT : 287.37

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

Summary Results:

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

Biotransformation Half-Life (days) : 0.0568 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): -0.03 (BAF = 0.939 L/kg wet-wt)

Log Kow (experimental): -0.21

Log Kow used by BCF estimates: -0.21

Equation Used to Make BCF estimate:

Log BCF = 0.50

Correction(s): Value

Correction Factors Not Used for Log Kow < 1

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

Validity criteria fulfilled:

not specified

Conclusions:

The bioconcentration factor (BCF) of 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS No. 6035-94-5) was estimated to be 3.162 L/kg whole body w.w (at 25 deg C).

Executive summary:

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS No. 6035-94-5). The bioconcentration factor (BCF) of 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 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 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS No. 6035-94-5). The bioconcentration factor (BCF) of 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate is not expected to bioaccumulate in the food chain.

Key value for chemical safety assessment

BCF (aquatic species):

30 162 dimensionless

Additional information

Following different studies includes predicted data and experimental study for the target chemical and the structurally similar read across to conclude the bioaccumulation of 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS No. 6035-94-5) in environment.

 

 

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS No. 6035-94-5). The bioconcentration factor (BCF) of 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which does not exceed the bioconcentration threshold of 2000, indicating that the chemical is not expected to bioaccumulate in the food chain.

 

Another study from the ACD DATABASE 2017 DONE Using Bio-concentration Factor (v12.1.0.50374) module Bio-concentration Factor over the entire pH scale (pH 0 -14) of the test substance 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS no. 6035 -94 -5) was estimated to be in a range of 1 -1.22. This value indicates that the test substance was considered to be non-accumulative in aquatic organisms.

 

Similar predicted data for the target chemical 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 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate was estimated to be 18.6 dimensionless. The predicted BCF result based on the 5 OECD principles. Thus based on the result it is concluded that the test substance 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate is non-bioaccumulative in nature.

 

The predicted data of the target chemical is supported by the structurally similar read across 2,2'-ethene-1,2-diylbis(5-aminobenzenesulfonic acid) (CAS: 81 -11 -8) from Japan chemical collaborative knowledge database (J check) 2017, indicates that

Bioaccumulation of 4,4'-diaminostilbene-2,2'-disulphonic acid was analyzed accpording to the OECD Guideline 305 C (Bioaccumulation: Test for the Degree of Bioconcentration in Fish). The test was carried out at nominal concentration of 1st Concentration area: 1 mg/L, 2nd Concentration area: 0.1 mg/L exposed to Cyprinus carpio for 6 wks. The Bioaccumulation factor(BCF) for 2,2'-ethene-1,2-diylbis(5-aminobenzenesulfonic acid (CAS: 81-11-8) is 4.7 L/kg in 6 wk.It can be concluded from the value that the, 2'-ethene-1,2-diylbis(5-aminobenzenesulfonic acid is not bioaccumulative in environment.

 

 

Further the experimental study for the structurally similar read across p-Aminodiphenylamine (CAS: 101-54-2) froom the publications Journal of Pharmaceutical Sciences 1995, Environmental Toxicology and Chemistry 1999 and Chemosphere 1994 suggests that An estimated BCF of 5.1 was calculated for p-aminodiphenylamine, using an estimated log Kow of 1.82(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the p-aminodiphenylamine is not bioaccumulative.

 

On the basis of above results for target chemical 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS No. 6035-94-5) (from EPI suite, CompTox Chemistry Dashboard) and for its read across chemical (from J-CHeck 2017and publications), and the value of BCF ranges from 1 -1.22 to 18.6 which does not exceed the bio-concentration threshold of 2000, it can be concluded that the chemical 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS No. 6035-94-5) is not expected to be bioaccumulate in the food chain.