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Bioaccumulation: aquatic / sediment

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Reference
Endpoint:
bioaccumulation in sediment species, other
Type of information:
(Q)SAR
Adequacy of study:
key study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Validated QSAR model
Justification for type of information:
QMRF and QPRF are given under overall remarks and executive summary, respectively.
Principles of method if other than guideline:
Calculation based on BCFBAF v3.01, Estimation Programs Interface Suite™ for Microsoft® Windows v 4.10. US EPA, United States Environmental Protection Agency, Washington, DC, USA.
GLP compliance:
no
Test organisms (species):
other: fish
Route of exposure:
aqueous
Test type:
other: calculation
Water / sediment media type:
natural water: freshwater
Details on estimation of bioconcentration:
BASIS FOR CALCULATION OF BCF
- Estimation software: BCFBAF v3.01
- Result based on calculated log Pow of: 16.24 (KOWWIN v1.68)
Key result
Type:
BCF
Value:
3.162 L/kg
Basis:
whole body w.w.
Remarks on result:
other: The substance is within the applicability domain of the BCFBAF submodel: Bioconcentration factor (BCF; Meylan et al., 1997/1999).
Key result
Type:
BCF
Value:
0.893 L/kg
Basis:
whole body w.w.
Calculation basis:
steady state
Remarks on result:
other: Upper trophic, incl. biotransformation estimates; The substance is within the applicability domain of the BCFBAF submodel: Arnot & Gobas BAF and steady-state BCF Arnot & Gobas, 2003).
Type:
BCF
Calculation basis:
steady state
Remarks on result:
other: Upper trophic, incl. biotransformation rate of zero; The substance is within the applicability domain of the BCFBAF submodel: Arnot & Gobas BAF and steady-state BCF Arnot & Gobas, 2003).
Type:
BAF
Basis:
not specified
Remarks on result:
other: Upper trophic, incl. biotransformation estimates; The substance is within the applicability domain of the BCFBAF submodel: Arnot & Gobas BAF and steady-state BCF Arnot & Gobas, 2003).
Type:
BAF
Basis:
not specified
Remarks on result:
other: Upper trophic, incl. biotransformation rate of zero; The substance is within the applicability domain of the BCFBAF submodel: Arnot & Gobas BAF and steady-state BCF Arnot & Gobas, 2003).
Details on kinetic parameters:
Biotransformation half-life (days): 2.97
Biotransformation rate (kM, normalised to 10 g fish at 15 °C): 933.3
The substance is within the applicability domain of the BCFBAF submodel: Biotransformation rate in fish (kM; Arnot et al., 2008a/b).

 BCFBAF Program (v3.01) Results:

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

SMILES : N(CCCCCCCCCCCC)(CCCCCCCCCCCC)CCCCCCCCCCCC

CHEM  : 1-Dodecanamine, N,N-didodecyl-

MOL FOR: C36 H75 N1

MOL WT : 522.01

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

Summary Results:

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

Biotransformation Half-Life (days) : 933 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): 0.02 (BAF = 1.05 L/kg wet-wt)

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 16.24

 

Equation Used to Make BCF estimate:

Log BCF = -0.49 log Kow + 7.554 + Correction

 

Correction(s):                   Value

No Applicable Correction Factors

Minimum Log BCF of 0.50 applied when Log Kow > 7

 

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

 

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

Whole Body Primary Biotransformation Rate Estimate for Fish:

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

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | LOG BIOTRANSFORMATION FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 3 | Linear C4 terminal chain [CCC-CH3]      | 0.0341 | 0.1024

Frag | 1 | Tertiary amine                           | -0.7829 | -0.7829

Frag | 3 | Methyl [-CH3]                           | 0.2451 | 0.7353

Frag | 33 | -CH2- [linear]                          | 0.0242 | 0.7982

L Kow| * | Log Kow = 16.24 (KowWin estimate)       | 0.3073 | 4.9927

MolWt| * | Molecular Weight Parameter               |        | -1.3386

Const| * | Equation Constant                        |        | -1.5058

============+============================================+=========+=========

RESULT  |       LOG Bio Half-Life (days)           |        | 2.9700

RESULT  |           Bio Half-Life (days)           |        |  933.3

NOTE    | Bio Half-Life Normalized to 10 g fish at 15 deg C  |

============+============================================+=========+=========

 

Biotransformation Rate Constant:

kM (Rate Constant): 0.0007427 /day (10 gram fish)

kM (Rate Constant): 0.0004177 /day (100 gram fish)

kM (Rate Constant): 0.0002349 /day (1 kg fish)

kM (Rate Constant): 0.0001321 /day (10 kg fish)

 

Arnot-Gobas BCF & BAF Methods (including biotransformation rate estimates):

Estimated Log BCF (upper trophic) = -0.049 (BCF = 0.893 L/kg wet-wt)

Estimated Log BAF (upper trophic) = 0.019 (BAF = 1.046 L/kg wet-wt)

Estimated Log BCF (mid trophic)  = -0.031 (BCF = 0.9315 L/kg wet-wt)

Estimated Log BAF (mid trophic)  = -0.001 (BAF = 0.9982 L/kg wet-wt)

Estimated Log BCF (lower trophic) = -0.027 (BCF = 0.9403 L/kg wet-wt)

Estimated Log BAF (lower trophic) = -0.011 (BAF = 0.9757 L/kg wet-wt)

 

Arnot-Gobas BCF & BAF Methods (assuming a biotransformation rate of zero):

Estimated Log BCF (upper trophic) = -0.049 (BCF = 0.893 L/kg wet-wt)

Estimated Log BAF (upper trophic) = 0.057 (BAF = 1.139 L/kg wet-wt)

 

 

Executive summary:

QPRF: BCFBAF v3.01

 

1.

Substance

See “Test material identity”

2.

General information

 

2.1

Date of QPRF

See “Data Source (Reference)”

2.2

QPRF author and contact details

See “Data Source (Reference)”

3.

Prediction

3.1

Endpoint
(OECD Principle 1)

Endpoint

Bioaccumulation (aquatic)

Dependent variable

- Bioconcentration factor (BCF)

- Bioaccumulation factor (BAF; 15 °C)

- Biotransformation rate (kM) and half-life

3.2

Algorithm
(OECD Principle 2)

Model or submodel name

BCFBAF

Submodels:

1) Bioconcentration factor (BCF; Meylan et al., 1997/1999)

2) Biotransformation rate in fish (kM; Arnot et al., 2008a/b)

3) Arnot & Gobas BAF and steady-state BCF Arnot & Gobas, 2003)

Model version

v. 3.01

Reference to QMRF

Estimation of Bioconcentration, bioaccumulation and biotransformation in fish using BCFBAF v3.01 (EPI Suite v4.11)

Predicted value (model result)

See “Results and discussion”

Input for prediction

Chemical structure via CAS number or SMILES; log Kow (optional)

Descriptor values

- SMILES: structure of the compound as SMILES notation

- log Kow

- Molecular weight

3.3

Applicability domain
(OECD principle 3)

Domains:

1) Bioconcentration factor (BCF; Meylan et al., 1997/1999)

a) Ionic/non-Ionic

The substance is non-ionic.

b) Molecular weight (range of test data set):

- Ionic: 68.08 to 991.80

- Non-ionic: 68.08 to 959.17

(On-Line BCFBAF Help File, Ch. 7.1.3 Estimation Domain and Appendix G)

The substance is within range (522.01 g/mol).

c) log Kow (range of test data set):

- Ionic: -6.50 to 11.26

- Non-ionic: -1.37 to 11.26

(On-Line BCFBAF Help File, Ch. 7.1.3 Estimation Domain and Appendix G)

The substance isnot within range (16.24).

 

d) Maximum number of instances of correction factor in any of the training set compounds (On-Line BCFBAF Help File, Appendix E)

Not applicable as correction factors were not used.

2) Biotransformation rate in fish (kM; Arnot et al., 2008a/b)

a) The substance does not appreciably ionize at physiological pH.

(On-Line BCFBAF Help File, Ch. 7.2.3)

fulfilled

b) Molecular weight (range of test data set): 68.08 to 959.17

(On-Line BCFBAF Help File, Ch. 7.2.3)

The substance is within range (522.01 g/mol).

c) The molecular weight is ≤ 600 g/mol.

(On-Line BCFBAF Help File, Ch. 7.2.3)

fulfilled

d) Log Kow: 0.31 to 8.70

(On-Line BCFBAF Help File, Ch. 7.2.3)

The substance isnot within range (16.24).

e) The substance isnometal or organometal, pigment or dye, or a perfluorinated substance.

(On-Line BCFBAF Help File, Ch. 7.2.3)

fulfilled

f) Maximum number of instances of biotransformation fragments in any of the training set compounds (On-Line BCFBAF Help File, Appendix F)

Not exceeded.

3) Arnot & Gobas BAF and steady-state BCF Arnot & Gobas, 2003)

a) Log Kow ≤ 9

(On-Line BCFBAF Help File, Ch. 7.3.1)

Not fulfilled

b) The substance does not appreciably ionize.

(On-Line BCFBAF Help File, Ch. 7.3.1)

fulfilled

c) The substance is no pigment, dye, or perfluorinated substance.

(On-Line BCFBAF Help File, Ch. 7.3.1)

fulfilled

3.4

The uncertainty of the prediction
(OECD principle 4)

1. Bioconcentration factor (BCF; Meylan et al., 1997/1999)

Statistical accuracy of the training data set (non-ionic plus ionic data):

- Correlation coefficient (r2) = 0.833

- Standard deviation = 0.502 log units

- Absolute mean error = 0.382 log units

 

2. Biotransformation Rate in Fish (kM)

Statistical accuracy (training set):

- Correlation coefficient (r2) = 0.821

- Correlation coefficient (Q2) = 0.753

- Standard deviation = 0.494 log units

- Absolute mean error = 0.383 log units

 

3. Arnot-Gobas BAF/BCF model

No information on the statistical accuracy given in the documentation.

3.5

The chemical mechanisms according to the model underpinning the predicted result
(OECD principle 5)

1. The BCF model is mainly based on the relationship between bioconcentration and hydrophobicity. The model also takes into account the chemical structure and the ionic/non-ionic character of the substance.

 

2. Bioaccumulation is the net result of relative rates of chemical inputs to an organism from multimedia exposures (e.g., air, food, and water) and chemical outputs (or elimination) from the organism.

 

3. The model includes mechanistic processes for bioconcentration and bioaccumulation such as chemical uptake from the water at the gill surface (BCFs and BAFs) and the diet (BAFs only), and chemical elimination at the gill surface, fecal egestion, growth dilution and metabolic biotransformation (Arnot and Gobas 2003). Other processes included in the calculations are bioavailability in the water column (only the freely dissolved fraction can bioconcentrate) and absorption efficiencies at the gill and in the gastrointestinal tract.

References

- Arnot JA, Gobas FAPC. 2003. A generic QSAR for assessing the bioaccumulation potential of organic chemicals in aquatic food webs. QSAR and Combinatorial Science 22: 337-345.

- Arnot JA, Mackay D, Parkerton TF, Bonnell M. 2008a. A database of fish biotransformation rates for organic chemicals. Environmental Toxicology and Chemistry 27(11), 2263-2270.

- Arnot JA, Mackay D, Bonnell M. 2008b.Estimating metabolic biotransformation rates in fish from laboratory data. Environmental Toxicology and Chemistry 27: 341-351.

- Meylan, W.M., Howard, P.H, Aronson, D., Printup, H. and S. Gouchie. 1997. "Improved Method for Estimating Bioconcentration Factor (BCF) from Octanol-Water Partition Coefficient", SRC TR-97-006 (2nd Update), July 22, 1997; prepared for: Robert S. Boethling, EPA-OPPT, Washington, DC; Contract No. 68-D5-0012; prepared by: ; Syracuse Research Corp., Environmental Science Center, 6225 Running Ridge Road, North Syracuse, NY 13212.

- Meylan, WM, Howard, PH, Boethling, RS et al. 1999. Improved Method for Estimating Bioconcentration / Bioaccumulation Factor from Octanol/Water Partition Coefficient. Environ. Toxicol. Chem. 18(4): 664-672 (1999). 

- US EPA (2012). On-Line BCFBAF Help File.

 

 

Identified Correction Factors (Appendix E), Biotransformation Fragments and Coefficient values (Appendix F)

 

Model: BCFBAF v3.01
Substance: Tridodecylamine
CAS: 102-87-4
SMILES: N(CCCCCCCCCCCC)(CCCCCCCCCCCC)CCCCCCCCCCCC
Ionic/Non-ionic non-ionic
Ionisation at physiological relevant pH Substance does not ionise appreciably at physiological relevant pH range.
Molecular Weight: 522,01
Log Kow: 16,24
         
Appendix E: BCF Non-Ionic Correction Factors Used by BCFBAF
The Training Set used to derive the BCF Correction Factors listed below contained a total of 431 compounds (see Appendix G for the compound list).  The number of compounds in the training set with logKow values of 1.0 to 7.0 total 396 compounds ... 35 training set compounds have a logKow value greater than 7.0 ... Compounds with logKow less than 1.0 were not used to derive correction factors.
Correction Factor   BCFBAF  No. compounds containing factor in training set Maximum number of each fragment in any individual compound No. of instances of each fragment for the current substance
Appendix F: kM Biotransformation Fragments & Coefficient Values .
The Training Set used to derive the Coefficient Values listed below contained a total of 421 compounds (see Appendix I for the compound list). .
Fragment Description Coefficient value No. compounds containing fragment in total training set Maximum number of each fragment in any individual compound No. of instances of each fragment for the current substance
Linear C4 terminal chain  [CCC-CH3]          0,03412373 43 3 3
Tertiary amine                                -0,78292477 5 2 1
Methyl  [-CH3]                                0,24510529 170 12 3
-CH2-  [linear]                              0,02418707 109 28 33
Assessment of applicability domain based on molecular weight and log Kow .
1. Bioconcentration Factor (BCF; Meylan et al., 1997/1999) .
Training set: Molecular weights Ionic Non-ionic .
Minimum 68,08 68,08 .
Maximum 991,80 959,17 .
Average 244,00 244,00 .
Assessment of molecular weight Molecular weight within range of training set. .
.
Training set: Log Kow Ionic Non-ionic .
Minimum -6,50 -1,37 .
Maximum 11,26 11,26 .
Assessment of log Kow Log Kow outside of range of training set. Therefore, the estimate may be less accurate. .
.
2. Biotransformation Rate in Fish (kM; Arnot et al., 2008a/b) .
Training set: Molecular weights .
Minimum 68,08 .
Maximum 959,17 .
Average 259,75 .
Assessment of molecular weight Molecular weight within range of training set. .
.
Training set: Log Kow .
Minimum 0,31 .
Maximum 8,70 .
Assessment of log Kow Log Kow outside of range of training set. Therefore, the estimate may be less accurate. .
.

 

Description of key information

Tridodecylamine does not accumulate in organisms.

Key value for chemical safety assessment

BCF (aquatic species):
3.1 L/kg ww

Additional information