(carboxymethyl)dimethyl-3-[(1-oxododecyl)amino]propylammonium hydroxide

Bioaccumulation: aquatic / sediment

Link to relevant study record(s)

Reference

Endpoint:

bioaccumulation in aquatic species, other

Type of information:

(Q)SAR

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

results derived from a valid (Q)SAR model and falling into its applicability domain, with limited documentation / justification

Justification for type of information:

1. SOFTWARE
US EPA. Estimation Programs Interface Suite™ for Microsoft® Windows. United States Environmental Protection Agency, Washington, DC, USA.

2. MODEL (incl. version number)
BCFWIN v2.15

3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL
C8: O=C(NCCCN1(CC(=O)O1)(C)C)CCCCCCC
C10: O=C(NCCCN1(CC(=O)O1)(C)C)CCCCCCCCC
C12: O=C(NCCCN1(CC(=O)O1)(C)C)CCCCCCCCCCC
C14: O=C(NCCCN1(CC(=O)O1)(C)C)CCCCCCCCCCCCC
C16: O=C(NCCCN1(CC(=O)O1)(C)C)CCCCCCCCCCCCCCC
C18: O=C(NCCCN1(CC(=O)O1)(C)C)CCCCCCCCCCCCCCCCC

4. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
see attachment

For Log Kow 1.0  to  7.0  the derived QSAR estimation equation is:
Log BCF  =  0.6598 Log Kow  -  0.333  + Σ correction factors
 (n = 396, r2 = 0.792, Q2 = 0.78, std dev = 0.511, avg dev = 0.395)

5. APPLICABILITY DOMAIN
Currently there is no universally accepted definition of model domain.  However, users may wish to consider the possibility that bioconcentration factor estimates are less accurate for compounds outside the MW and logKow ranges of the training set compounds, and/or that have more instances of a given correction factor than the maximum for all training set compounds.  It is also possible that a compound may have a functional group(s) or other structural features not represented in the training set, and for which no fragment coefficient was developed; and that a compound has none of the fragments in the model’s fragment library.  In the latter case, predictions are based on molecular weight alone.  These points should be taken into consideration when interpreting model results.

Training Set (527 Compounds):
Molecular Weight:
 Minimum MW:  68.08  (Furan)
 Maximum MW:  991.80   Ionic: (2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6- bis[[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]azo]-, tetrasodium salt)
 Maximum MW:  959.17   Non-Ionic: (Benzene, 1,1 -oxybis[2,3,4,5,6-pentabromo-)
 Average MW:  244.00
Log Kow:
 Minimum LogKow:  -6.50   Ionic: (2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]azo]-, tetrasodium salt)
 Minimum LogKow:  -1.37   Non-Ionic: (1,3,5-Triazine-2,4,6-triamine)
 Maximum LogKow:  11.26 (Benzenamine, ar-octyl-N-(octylphenyl)-)

6. ADEQUACY OF THE RESULT
The result is considered to be adequate for hazard assessment purposes.

Qualifier:

no guideline followed

Principles of method if other than guideline:

The authors collected measured BCF (sources: AQUIRE, CITI, HSDB and EFDB), log Kow (sources: MEDCHEM 'star list', Sangster's LOGKOW DATABANK or sources referenced in the EFDB or KOWWIN estimates), and pKa values for ionizing substances (sources: SRC's PHYSPROP database, compilation of Perrin and Serjeant and Dempsey and reference handbooks such as Handbook of Organic Chemistry, the Handbook of Chemistry and Physics and other sources cited in the EFDB or calculated using pKalc 3.1 software or SPARC. The database of 694 compounds with recommended BCF values contained 84 compounds defined as ionic, including carboxylic acids, sulfonic acids, and quaternary ammonium compounds. Based on the correlation of measured log BCF values and log Kow, log BCF values were deduced. The results were used to develop the computer program BCFWIN. BCFWIN v2.15 was used to calculate the BCF values for AAPB.

GLP compliance:

no

Radiolabelling:

no

Test organisms (species):

other: fish

Route of exposure:

aqueous

Test type:

other: calculation

Water / sediment media type:

natural water: freshwater

Reference substance (positive control):

not required

Type:

BCF

Value:

3

Remarks on result:

other: C8 derivates of AAPB

Type:

BCF

Value:

71

Remarks on result:

other: C10 - C18 and C18 unsaturated derivates of AAPB

The authors collected measured BCF (sources: AQUIRE, CITI, HSDB and EFDB), 
log Kow (sources: MEDCHEM 'star list', Sangster's LOGKOW DATABANK or sources 
referenced in the EFDB or KOWWIN estimates), and pKa values for ionizing 
substances (sources: SRC's PHYSPROP database, compilation of Perrin and 
Serjeant and Dempsey and reference handbooks such as Handbook of Organic 
Chemistry, the Handbook of Chemistry and Physics and other sources cited in the 
EFDB or calculated using pKalc 3.1 software or SPARC. The database of 694 
compounds with recommended BCF values contained 84 compounds defined as ionic, 
including carboxylic acids, sulfonic acids, and quaternary ammonium compounds. 
Based on the correlation of measured log BCF values and log Kow, log BCF values 
were deduced. The results were used to develop the computer program BCFWIN. 
Therefore, BCFWIN v2.15 was used to calculate the BCF values for the C8-C18 
derivates of AAPB. The calculation yielded values in the range between
3 (C8 fatty acid derivate) and 71 (C10 -C18 and C18 unsaturated fatty acid 
derivates).

Validity criteria fulfilled:

not applicable

Conclusions:

The calculation of BCFs via BCFWIN v2.15 for the C8-C18 fatty acid derivates yielded values in the range between 3 (C8 fatty acid derivate) and 71 (C10 – C18 and C18 unsaturated fatty acid derivates). Based on the calculated BCFs a low potential for bioaccumulation is to be expected for AAPB.

Executive summary:

The authors collected measured BCF (sources: AQUIRE, CITI, HSDB and EFDB), log Kow (sources: MEDCHEM 'star list', Sangster's LOGKOW DATABANK or sources referenced in the EFDB or KOWWIN estimates), and pKa values for ionizing substances (sources: SRC's PHYSPROP database, compilation of Perrin and Serjeant and Dempsey and reference handbooks such as Handbook of Organic Chemistry, the Handbook of Chemistry and Physics and other sources cited in the EFDB or calculated using pKalc 3.1 software or SPARC. The database of 694 compounds with recommended BCF values contained 84 compounds defined as ionic, including carboxylic acids, sulfonic acids, and quaternary ammonium compounds. Based on the correlation of measured log BCF values and log Kow, log BCF values were deduced. The results were used to develop the computer program BCFWIN. Therefore, BCFWIN v2.15 was used to calculate the BCF values for the C8-C18 derivates of AAPB. The calculation yielded values in the range between 3 (C8 fatty acid derivate) and 71 (C10 – C18 and C18 unsaturated fatty acid derivates). Based on the calculated BCFs a low potential for bioaccumulation is to be expected for AAPB.

Description of key information

The calculation of BCFs  via BCFWIN v2.15 for the C8-C18 fatty acid derivates yielded values in the range between 3 (C8 fatty acid derivate) and 71 (C10 – C18 and C18 unsaturated fatty acids derivates). Based on the calculated BCFs a low potential for bioaccumulation is to be expected  AAPBs.

Key value for chemical safety assessment

BCF (aquatic species):

71 dimensionless

Additional information

No experimental results for bioaccumulation with AAPBs are available. Considering the ready biodegradability, demonstrating the ability of organisms to metabolize AAPB, a relevant bioaccumulation potential of AAPB is not expected. This expectation is also supported by a modelling approach performed by Meylan et al. (1999). To develop a model on bioaccumulation, Meylan et al. (1999) collected measured BCF (sources: AQUIRE, CITI, HSDB and EFDB), log Kow (sources: MEDCHEM 'star list', Sangster's LOGKOW DATABANK or sources referenced in the EFDB or KOWWIN estimates), and pKa values for ionizing substances (sources: SRC's PHYSPROP database, compilation of Perrin and Serjeant and Dempsey and reference handbooks such as Handbook of Organic Chemistry, the Handbook of Chemistry and Physics and other sources cited in the EFDB or calculated using pKalc 3.1 software or SPARC). The database of 694 compounds with recommended BCF values contained 84 compounds defined as ionic, including carboxylic acids, sulfonic acids, and quaternary ammonium compounds. Based on the correlation of measured log BCF values and log Kow, log BCF values were deduced. The results were used to develop the computer program BCFWIN. Therefore, BCFWIN v2.15 was used to calculate the BCF values for the C8-C18 derivates of AAPB. The calculation yielded values in the range between 3 (C8 fatty acid derivate) and 71 (C10 – C18 and C18 unsaturated fatty acid derivates). Based on the calculated BCFs a low potential for bioaccumulation is to be expected for AAPBs. Measured BCFs are not available.