2-Propenoic acid, 2-methyl-, heptadecyl ester, branched

Bioaccumulation: aquatic / sediment

Administrative data

Endpoint:

bioaccumulation: aquatic / sediment

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Scientifically accepted calculation method

Justification for type of information:

QSAR prediction: migrated from IUCLID 5.6

Data source

Reference

Reference 1

Reference Type:

other: Estimation software

Title:

Estimation Programs Interface Suite for Microsoft Windows, v4.11

Author:

US EPA

Year:

2012

Bibliographic source:

United States Environmental Protection Agency, Washington, DC, USA; November 2012

Reference 2

Reference Type:

other: EPIWIN calculation

Title:

Unnamed

Year:

2015

Materials and methods

Principles of method if other than guideline:

Estimation of BCF, BAF and biotransformation rate using BCFBAF v3.01

Test material

Test material information

Constituent 1

Reference substance name:

CCCCCCCCCCCCCCCCCOC(=O)C(C)=C

IUPAC Name:

CCCCCCCCCCCCCCCCCOC(=O)C(C)=C

Results and discussion

Bioaccumulation factor

Bioaccumulation factor 1

Type:

BCF

Value:

304 L/kg

Basis:

not specified

Remarks on result:

other: The substance is within the applicability domain of the BCFBAF submodel: Bioconcentration factor (BCF; Meylan et al., 1997/1999).

Bioaccumulation factor 2

Type:

BCF

Value:

9.681 L/kg

Basis:

not specified

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).

Bioaccumulation factor 3

Type:

BCF

Value:

551.9 L/kg

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).

Details on kinetic parameters:

Biotransformation half-life (days): 6.11
Biotransformation rate (kM, normalised to 10 g fish at 15 °C): 0.1134/day
The substance is within the applicability domain of the BCFBAF submodel: Biotransformation rate in fish (kM; Arnot et al., 2008a/b).

Any other information on results incl. tables

Summary Results:

Log BCF (regression-based estimate): 2.48 (BCF = 304 L/kg wet-wt)

Biotransformation Half-Life (days) : 6.11 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): 2.76 (BAF = 569 L/kg wet-wt)

 

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 9.13

 

Equation Used to Make BCF estimate:

Log BCF = -0.49 log Kow + 7.554 + Correction

 

Correction(s):                   Value

Alkyl chains (8+ -CH2- groups) -0.596

 

Estimated Log BCF = 2.482 (BCF = 303.7 L/kg wet-wt)

 

 

Whole Body Primary Biotransformation Rate Estimate for Fish:

 

 

TYPE	NUM	LOG BIOTRANSFORMATION FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Linear C4 terminal chain [CCC-CH3]	0.0341	0.0341
Frag	1	Ester  [-C(=O)-O-C]	-0.7605	-0.7605
Frag	2	Methyl [-CH3]	0.2451	0.4902
Frag	16	-CH2- [linear]	0.0242	0.3870
Frag	2	-C=CH [alkenyl hydrogen]	0.0988	0.1977
Frag	2	-C=CH [alkenyl hydrogen]	0.0000	0.0000
L Kow	*	Log Kow =  9.13 (KowWin estimate)	0.3073	2.8069
MolWt	*	Molecular Weight Parameter		-0.8323
Const	*	Equation Constant		-1.5371
RESULT	LOG Bio Half-Life (days)  0.7860
RESULT	Bio Half-Life (days)  6.11
NOTE	Bio Half-Life Normalized to 10 g fish at 15 deg C

 

Biotransformation Rate Constant:

kM (Rate Constant): 0.1134 /day (10 gram fish)

kM (Rate Constant): 0.0638 /day (100 gram fish)

kM (Rate Constant): 0.03588 /day (1 kg fish)

kM (Rate Constant): 0.02017 /day (10 kg fish)

 

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

Estimated Log BCF (upper trophic) = 0.986 (BCF = 9.681 L/kg wet-wt)

Estimated Log BAF (upper trophic) = 2.755 (BAF = 569.3 L/kg wet-wt)

Estimated Log BCF (mid trophic)  = 1.115 (BCF = 13.03 L/kg wet-wt)

Estimated Log BAF (mid trophic)  = 3.247 (BAF = 1768 L/kg wet-wt)

Estimated Log BCF (lower trophic) = 1.155 (BCF = 14.28 L/kg wet-wt)

Estimated Log BAF (lower trophic) = 3.539 (BAF = 3458 L/kg wet-wt)

 

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

Estimated Log BCF (upper trophic) = 2.742 (BCF = 551.9 L/kg wet-wt)

Estimated Log BAF (upper trophic) = 6.435 (BAF = 2.721e+006 L/kg wet-wt)

Applicant's summary and conclusion

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 isnon-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 iswithin range (310 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 is within range
		d) Maximum number of instances of correction factor in any of the training set compounds (On-Line BCFBAF Help File, Appendix E)
		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 iswithin range (310 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)	log Pow 9
		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)	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 (r^2) = 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 (r^2) = 0.821 - Correlation coefficient (Q^2) = 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.