3-hydroxy-4-[(2-methoxy-5-nitrophenyl)azo]-N-(3-nitrophenyl)naphthalene-2-carboxamide

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 : 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide
- Common name : 3-hydroxy-4-[(2-methoxy-5-nitrophenyl)azo]-N-(3-nitrophenyl)naphthalene-2-carboxamide, C.I. Pigment Red 23
- Molecular formula : C24H17N5O7
- Molecular weight : 487.4263 g/mol
- Smiles notation : c12c(c(c(cc1cccc2)C(=O)Nc1cc(ccc1)[N+](=O)[O-])O)/N=N/c1c(ccc(c1)[N+](=O)[O-])OC
- InChl : 1S/C24H17N5O7/c1-36-21-10-9-17(29(34)35)13-20(21)26-27-22-18-8-3-2-5-14(18)11-19(23(22)30)24(31)25-15-6-4-7-16(12-15)28(32)33/h2-13,30H,1H3,(H,25,31)/b27-26+
- 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:

10 L/kg

Basis:

whole body w.w.

Calculation basis:

other: estimated

Remarks on result:

other: Non-bioaccumulative

BCFBAF Program (v3.01) Results:

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

SMILES : O=C(Nc(cccc1N(=O)(=O))c1)c(c(O)c(N=Nc(c(OC)ccc2N(=O)(=O))c2)c(c3ccc4)

c4)c3

CHEM : 2-Naphthalenecarboxamide, 3-hydroxy-4- (2-methoxy-5-nitrophenyl)azo -

N-(3-nitrophenyl)-

MOL FOR: C24 H17 N5 O7

MOL WT : 487.43

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

Summary Results:

Log BCF (regression-based estimate): 1.00 (BCF = 10 L/kg wet-wt)

Biotransformation Half-Life (days) : 2.8 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): 2.57 (BAF = 375 L/kg wet-wt)

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 8.30

Equation Used to Make BCF estimate:

Log BCF = 1.00 { Aromatic Azo Specification }

Correction(s): Value

Aromatic Azo compound 0.000

Estimated Log BCF = 1.000 (BCF = 10 L/kg wet-wt)

Validity criteria fulfilled:

not specified

Conclusions:

The bioconcentration factor (BCF) of 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide was estimated to be 10 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide 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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl) diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide (CAS No. 6471 -49 -4). The bioconcentration factor (BCF) of 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide was estimated to be 10 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide 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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl) diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide (CAS No. 6471 -49 -4). The bioconcentration factor (BCF) of 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide was estimated to be 10 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide is not expected to bioaccumulate in the food chain.

Key value for chemical safety assessment

BCF (aquatic species):

10 L/kg ww

Additional information

Various predicted data for the target compound 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (CAS No. 6471-49-4) 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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl) diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide (CAS No. 6471 -49 -4). The bioconcentration factor (BCF) of 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide was estimated to be 10 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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide was estimated to be 107 dimensionless . The predicted BCF result based on the 5 OECD principles.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017) for the read across chemical 1-(4-Methyl-2-nitrophenylazo)-2-naphthol (CAS no. 2425-85-6),bioaccumulation experiment was conducted on test organism Cyprinus carpio for 6 weeks for evaluating the bioconcentration factor (BCF value) of 1-(4-Methyl-2-nitrophenylazo)-2-naphthol.The study was performed according to “OECD Guideline 305 C (Bioaccumulation: Test for the Degree of Bioconcentration in Fish)” and other guideline "Bioaccumulation test of a chemical substance in fish or shellfish" provided in "the Notice on the Test Method Concerning New Chemical Substances", respectively. Cyprinus carpio was used as a test organism for the study. Test chemical nominal conc. used for the study were 1 mg/land 0.1 mg/l, respectively. Test chemical solution was prepared in crystal sugar or HCO-40.Analytical method involve the recovery ratio: Fish : 85.8 %, - Limit of quantitation : Test water : 1st concentration area : 0.024 mg/L, 2nd concentration area : 0.0024 mg/L, Fish : 0.28 microg/g. Range finding study involve the LC50 (48hr) ≥ 400 mg/l on Rice fish (Oryzias latipes). Lipid content of the test organism Cyprinus carpio was determined to be4.2% at start of exposure. The bioconcentration factor (BCF value) of substance 1-(4-Methyl-2-nitrophenylazo)-2-naphthol on Cyprinus carpio was determined to be in the range of 0.3 – 2.7 L/Kg at a conc. of 1 mg/l and ≤ 2.9 L/Kg at a conc. of 0.1 mg/l, respectively.

 

Another bioaccumulation study was conducted for estimating the BCF (bioaccumulation factor) value of the same read across chemical 1-(4-Methyl-2-nitrophenylazo)-2-naphthol (CAS no. 2425-85-6) (HSDB, 2017). The bioaccumulation factor (BCF) value was calculated using alog Kow of 6.5 and a regression-derived equation. The estimated BCF (bioaccumulation factor) value of 1 -(4 -Methyl-2 -nitrophenylazo)-2 -naphthol was determined to be 10 dimensionless.

 

For the read across chemical 1-[(2-chloro-4-nitrophenyl)azo]-2-naphthol (CAS no. 2814-77-9),bioaccumulation study was conducted for estimating the BCF (bioaccumulation factor) value of read across chemical 1-[(2-chloro-4-nitrophenyl)azo]-2-naphthol (HSDB, 2017). The bioaccumulation factor (BCF) value was calculated using a log Kow of 6.6 and a regression-derived equation. The estimated BCF (bioaccumulation factor) valueof 1-[(2-chloro-4-nitrophenyl)azo]-2-naphthol was determined to be 10 dimensionless.

 

On the basis of above results for target chemical 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (from EPI suiteand CompTox Chemistry Dashboard,  2017) and for its read across substance (from authoritative database J-CHECK and HSDB), it can be concluded that the BCF value of test substance3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamideranges from 10 – 107 which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide is not expected to bioaccumulate in the food chain.