Exo-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptan-2-ol

Biodegradation in water: screening tests

Administrative data

Endpoint:

biodegradation in water: ready biodegradability

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 adequate and reliable documentation / justification

Justification for type of information:

Please refer to QMRF and QPRF in the section "Overall remarks" and "Executive summary", respectively.

Data source

Reference

Reference 1

Reference Type:

other: EPIWin calculation

Title:

Unnamed

Year:

2017

Report date:

2017

Reference 2

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

Materials and methods

Test guideline

Qualifier:

no guideline followed

Principles of method if other than guideline:

Prediction of ready biodegradability based on EPI Suite v4.11 BIOWIN v4.10.

GLP compliance:

no

Test material

Test material information

Constituent 1

Reference substance name:

(1S,2S)-1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptan-2-ol

Cas Number:

87172-89-2

IUPAC Name:

(1S,2S)-1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptan-2-ol

Test material form:

solid

Results and discussion

% Degradation

% Degradation 1

Key result

Remarks on result:

other: Ready biodegradability prediction: Substance is not readily biodegradable.

% Degradation 2

Key result

Remarks on result:

other: Biowin1: Does not biodegrade fast; Biowin2: Does not biodegrade fast; Biowin3: Weeks-Months; Biowin4: Days-Weeks; Biowin5: Biodegrades fast; BIOWIN6: Does not biodegrade fast

Any other information on results incl. tables

BIOWIN (v4.10) Program Results:

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

SMILES : CC(C)C12CCC(O1)(C(C2)O)C

MOL FOR: C10 H18 O2

MOL WT : 170.25

 

--------------------------- BIOWIN v4.10 Results ----------------------------

Biowin1 (Linear Model Prediction): Does Not Biodegrade Fast

Biowin2 (Non-Linear Model Prediction): Does Not Biodegrade Fast

Biowin3 (Ultimate Biodegradation Timeframe): Weeks-Months

Biowin4 (Primary Biodegradation Timeframe): Days-Weeks

Biowin5 (MITI Linear Model Prediction): Biodegrades Fast

Biowin6 (MITI Non-Linear Model Prediction): Does Not Biodegrade Fast

Biowin7 (Anaerobic Model Prediction): Does Not Biodegrade Fast

Ready Biodegradability Prediction: NO

 

TYPE	NUM	Biowin1 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Aliphatic alcohol [-OH]	0.1587	0.1587
Frag	2	Carbon with 4 single bonds & no hydrogens	-0.1839	-0.3679
Frag	1	Aliphatic ether [C-O-C]	-0.3474	-0.3474
MolWt	*	Molecular Weight Parameter		-0.0811
Const	*	Equation Constant		0.7475
RESULT	Biowin1 (Linear Biodeg Probability)			0.1100

 

TYPE	NUM	Biowin2 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Aliphatic alcohol [-OH]	1.1178	1.1178
Frag	2	Carbon with 4 single bonds & no hydrogens	-1.7232	-3.4464
Frag	1	Aliphatic ether [C-O-C]	-3.4294	-3.4294
MolWt	*	Molecular Weight Parameter		-2.4176
RESULT	Biowin2 (Non-Linear Biodeg Probability)			0.0057

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

 

TYPE	NUM	Biowin3 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Aliphatic alcohol [-OH]	0.1600	0.1600
Frag	2	Carbon with 4 single bonds & no hydrogens	-0.2121	-0.4242
Frag	1	Aliphatic ether [C-O-C]	-0.0087	-0.0087
MolWt	*	Molecular Weight Parameter		-0.3762
Const	*	Equation Constant		3.1992
RESULT	Biowin3 (Survey Model - Ultimate Biodeg)			2.5500

 

TYPE	NUM	Biowin4 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Aliphatic alcohol [-OH]	0.1294	0.1294
Frag	2	Carbon with 4 single bonds & no hydrogens	-0.1534	-0.3069
Frag	1	Aliphatic ether [C-O-C]	-0.0097	-0.0097
MolWt	*	Molecular Weight Parameter		-0.2456
Const	*	Equation Constant		3.8477
RESULT	Biowin4 (Survey Model - Primary Biodeg)		3.4149

Result Classification: 5.00 -> hours 4.00 -> days 3.00 -> weeks

(Primary & Ultimate) 2.00 -> months 1.00 -> longer

 

TYPE	NUM	Biowin5 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Aliphatic alcohol [-OH]	0.1611	0.1611
Frag	2	Carbon with 4 single bonds & no hydrogens	0.0676	0.1352
Frag	1	Aliphatic ether [C-O-C]	0.0015	0.0015
Frag	3	Methyl [-CH3]	0.0004	0.0012
Frag	1	-CH- [linear]	-0.0507	-0.0507
Frag	3	-CH2- [cyclic]	0.0197	0.0592
Frag	1	-CH - [cyclic]	0.0124	0.0124
MolWt	*	Molecular Weight Parameter		-0.5065
Const	*	Equation Constant		0.7121
RESULT	Biowin5 (MITI Linear Biodeg Probability)		0.5257

 

TYPE	NUM	Biowin6 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Aliphatic alcohol [-OH]	1.0041	1.0041
Frag	2	Carbon with 4 single bonds & no hydrogens	0.3990	0.7980
Frag	1	Aliphatic ether [C-O-C]	-0.1071	-0.1071
Frag	3	Methyl [-CH3]	0.0194	0.0583
Frag	1	-CH- [linear]	-0.0998	-0.0998
Frag	3	-CH2- [cyclic]	0.2365	0.7096
Frag	1	-CH - [cyclic]	-0.1295	-0.1295
MolWt	*	Molecular Weight Parameter		-4.9150
RESULT	Biowin6 (MITI Non-Linear Biodeg Probability)		0.4611

A Probability Greater Than or Equal to 0.5 indicates --> Readily Degradable

A Probability Less Than 0.5 indicates --> NOT Readily Degradable

 

Ready Biodegradability Prediction: (YES or NO)

----------------------------------------------

Criteria for the YES or NO prediction: If the Biowin3 (ultimate survey model) result is "weeks" or faster (i.e. "days", "days to weeks", or "weeks" AND the Biowin5 (MITI linear model) probability is >= 0.5, then the prediction is YES (readily biodegradable). If this condition is not satisfied, the prediction is NO (not readily biodegradable). This method

is based on application of Bayesian analysis to ready biodegradation data. Biowin5 and 6 also predict ready biodegradability, but for degradation in the OECD301C test only; using data from the Chemicals Evaluation and Research Institute Japan (CERIJ) database.

Applicant's summary and conclusion

Interpretation of results:

not readily biodegradable

Executive summary:

QPRF: BIOWIN v4.10

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				Biodegradability
		Dependent variable				Biodegradability
3.2	Algorithm (OECD Principle 2)	Model or submodel name				BIOWIN
		Model version				v. 4.10
		Reference to QMRF				QMRF: Estimation of Aerobic Biodegradability using BIOWIN v4.10 (EPI Suite v4.11): BIOWIN1 to BIOWIN6 and Ready Biodegradability Prediction
		Predicted value (model result)				See “Results and discussion”
		Input for prediction				- Chemical structure via CAS number or SMILES
		Descriptor values				- Structure fragments - Molecular weight
3.3	Applicability domain (OECD principle 3)	Domains (Appendix D, On-Line BIOWIN User’s Guide):
		1) Molecular weight				See below (Assessment of estimation domain)
		2) Fragments:				See below (Assessment of estimation domain)
3.4	The uncertainty of the prediction (OECD principle 4)	Parameter	BIOWIN model
			1	2	3		4	5	6
		Total correct	264 / 295	275 / 295	167 / 200		165 / 200	485 / 589	488 / 589
		% correct, total	89.5	93.2	83.5		82.5	82.3	82.9
		% correct, fast	97.3 (181 / 186)	97.3 (181 / 186)	93.5 (101 / 108)		84.9 (101 / 119)	79.1 (201 / 254)	80.3 (204 / 254)
3.5	The chemical mechanisms according to the model underpinning the predicted result (OECD principle 5)	The chemical structure influences the biodegradability of the substance. Therefore, chemical fragments were selected having a potential effect on biodegradability. In order to be able to predict the biodegradability probability of substances without these specific fragments, the molecular weight was integrated into the models.

References

- US EPA (2012). On-Line BIOWIN User’s Guide.

  

Assessment of estimation domain (molecular weight, fragments):

Model:	BIOWIN v4.10
CAS-#:	87172-89-2
SMILES:	CC(C)C12CCC(O1)(C(C2)O)C
Molecular weight (g/mol):	170.25

 

AppendixD - Fragment Coefficients for Biodegradation Models

BIOWIN1 and BIOWIN2: Linear / Non-Linear Biodegradability

Fragment description	Coefficient		Training set fragment count			No. of instances of each bond found for the current substance
	Linear	Non-linear	Min	Max	No. of compounds in training set containing the fragment
Aliphatic alcohol [-OH]	0.15873	1.1178	-	3	34	1
Carbon with 4 single bonds & no hydrogens	-0.18393	-1.7232	-	2	9	2
Aliphatic ether [C-O-C]	-0.34736	-3.4294	-	2	11	1
Molecular Weight	---	---	31.06	697.7		in range

 

BIOWIN3 and BIOWIN4: Ultimate / Primary biodegradability

Fragment description	Coefficient		Training set fragment count			No. of instances of each bond found for the current substance
	Ultimate	Primary	Min	Max	No. of compounds in training set containing the fragment
Aliphatic alcohol [-OH]	0.15997	0.12945	-	4	18	1
Carbon with 4 single bonds & no hydrogens	-0.21212	-0.15344	-	3	32	2
Aliphatic ether [C-O-C]	-0.00867	-0.00974	-	5	16	1
Molecular Weight	---	---	53.06	697.65	-	in range

 

 BIOWIN5 and BIOWIN6: MITI Biodegradability Coefficients (Linear / Non-Linear)

Fragment description	Coefficient		Training set fragment count			No. of instances of each bond found for the current substance
	Linear	Non-Linear	Min	Max	No. of compounds in training set containing the fragment
Aromatic alcohol [-OH]	0.064226	0.48842336	-	2	65	1
Carbon with 4 single bonds & no hydrogens	0.067617	0.39898879	-	9	53	2
Aliphatic ether [C-O-C]	0.00147	-0.10714727	-	3	34	1
Methyl [-CH3]	0.000411	0.01942827	-	9	295	3
-CH- [linear]	-0.050672	-0.09977022	-	4	63	1
-CH2- [cyclic]	0.019727	0.2365247	-	12	62	3
-CH - [cyclic]	0.012444	-0.12945411	-	6	47	1
Molecular Weight	---	---	30.02	959.2	-	in range