7-acetamido-4-hydroxy-3-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]naphthalene-2-sulphonic acid

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:

Data is from computational model developed by 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 the test material: 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid
- IUPAC name: 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid
- Molecular formula: C20H19N3O11S3
- Molecular weight: 573.578 g/mol
- Smiles: c1c(c(c(c2ccc(cc12)NC(=O)C)O)\N=N\c1ccc(cc1)S(=O)(=O)CCOS(=O)(=O)O)S(=O)(=O)O
-InChI:1S/C20H19N3O11S3/c1-12(24)21-15-4-7-17-13(10-15)11-18(36(28,29)30)19(20(17)25)23-22-14-2-5-16(6-3-14)35(26,27)9-8-34-37(31,32)33/h2-7,10-11,25H,8-9H2,1H3,(H,21,24)(H,28,29,30)(H,31,32,33)/b23-22+
- Substance type: Organic
- Physical state: Solid

Radiolabelling:

not specified

Vehicle:

not specified

Test organisms (species):

other: Fish

Route of exposure:

aqueous

Test type:

other: estimation

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 : O=C(Nc(ccc(c1cc(S(=O)(=O)O)c2N=Nc(ccc(S(=O)(=O)CCOS(=O)(=O)O)c3)c3)c2

O)c1)C

CHEM : 2-Naphthalenesulfonic acid, 7-(acetylamino)-4-hydroxy-3- 4- 2-(sulf

ooxy)ethyl sulfonyl phenyl azo -

MOL FOR: C20 H19 N3 O11 S3

MOL WT : 573.57

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

Summary Results:

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

Biotransformation Half-Life (days) : 0.000162 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): -0.05 (BAF = 0.893 L/kg wet-wt)

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: -3.30

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:

Using BCFBAF Program (v3.00) model of EPI suite (2017) the estimated bio concentration factor (BCF) for 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid (CAS No.68189-39-9) is 3.162L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000. Therefore it is concluded that test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid is non bioaccumulative in food chain.

Executive summary:

Using BCFBAF Program (v3.00) model of EPI suite (2017) the estimated bio concentration factor (BCF) for 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  (CAS No.68189-39-9) is 3.162L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000. Therefore it is concluded that test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  is non bioaccumulative in food chain.

Description of key information

Using BCFBAF Program (v3.00) model of EPI suite (2017) the estimated bio concentration factor (BCF) for 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  (CAS No.68189-39-9) is 3.162L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000. Therefore it is concluded that test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  is non bioaccumulative in food chain.

Key value for chemical safety assessment

BCF (aquatic species):

3.162 L/kg ww

Additional information

Various predicted data for the target compound7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  (CAS No.68189-39-9)and supporting weight of evidence study for its read across chemical were reviewed for the bioaccumulation end point which are summarized as below:

First weight of evidence studies for target chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  (CAS No.68189-39-9) done by using BCFBAF Program (v3.00) model of Estimation Program Interface (EPI suite 2017) in this study the estimated bio concentration factor (BCF) for target chemical is 3.162L/kg wet-wt at 25 deg. c

 

Second weight of evidence study was done by Using Bio-concentration Factor (v12.1.0.50374) module of Advanced Chemistry Develpoment /I lab predictive module (2017) in this study the Bio-concentration Factor at range pH 1-14  of the test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid (CAS no.68189 -39 -9) estimated to be 1.0 dimensionless.

Third weight of evidence study was done by using Scifinder database of American Chemical Society ( ACS, 2017) in this study the Bioconcentration factor (BCF) for test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid   was predicted in aquatic organisms by at pH 1-10 and temperature 25 °C .The Bioconcentration factor (BCF) of test substance at pH 1-10 and temperature 25 °C was estimated to be 1.0 dimensionless.  

 

Fourth weight of evidence study was done by using Chemspider- ACD/PhysChem Suite of Royal Society of Chemistry, 2017 in this study the Bioconcentration factor (BCF) for test chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  (CAS No: 68189-39-9) was predicted in aquatic organisms by  at pH 5.5 and pH 7.4. The Bioconcentration factor (BCF) of test chemical at pH 5.5 and pH 7.4 was estimated to be 1.0 dimensionless. 

 

Next study was done 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 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid was estimated to be 2.31 dimensionless. The predicted BCF result was based on the 5 OECD principles.

 

Last weight of evidence study was done for structurally similar read across chemical chemical2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4)(CAS no 17095-24-8) from authoritative database J check, 2017 in this study the Bioaccumulation test was conducted for 6 weeks for determination the bioconcentration factor (BCF) of read across chemical on test organism Cyprinus carpio. In this test Recovery ratio used was Test water: 1st concentration area: 98.4 %, 2nd concentration area : 95.4 %, Fish : 62.2 %, - Limit of detection : Test water 1st concentration area : 0.15 ppm, 2nd concentration area : 0.016 ppm, Fish : 2.1 ppm and

Nominal concentrations used in the study are 1st Concentration area: 2.0 mg/L, 2nd Concentration area: 0.2 mg/L and Range finding study was carried out on Rice fish (Oryzias latipes) TLm(48h) >= 1000 ppm(w/v). The lipid content of fish was 4.7 %.

Thus according to static Fish Test the BCF value 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4) was observed to be≤ 1.1 L/kg at dose concentration 2.0 mg/L and ≤ 11 L/kg at dose concentration 0.2 mg/L  on the basis of lipid content on test organism Cyprinus carpio during 6 weeks period. These BCF values indicate that the read across substance 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4) is not bioaccumulative in fish and food chain as these values are far less than 2000 criteria.

 

On the basis of above results for target chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  (from EPI suite, ACD labs, Sci Finder database, Chemspider and CompTox Chemistry Dashboard, 2017) and for its read across chemicals (From J check) it can be concluded that the BCF value of test substance 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  ranges from 1 to 3.162 dimensionless which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 7-acetamido-4-hydroxy-3-[(E)-2-{4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]naphthalene-2-sulfonic acid  is expected to be non bioaccumulative in the food chain.