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Reference
Endpoint:
adsorption / desorption: screening
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:
(Q)SAR prediction from a well-known and acknowledged tool.
Qualifier:
according to guideline
Guideline:
other: REACH guidance on QSARs: Chapter R.6. QSARs and grouping of chemicals
Principles of method if other than guideline:
Since the test substance is a UVCB with similar constituents varying mainly in carbon chain lengths, the Koc values were estimated for the individual components using the MCI (Molecular Connectivity Index) approach of the KOCWIN v2.00 program followed by the determination of an overall weighted-average value using the mole fractions of all the individual components.
Computational methods:
Since the test substance is an UVCB with several constituents varying mainly in carbon chain lengths, the Koc values were estimated for the individual components using the MCI (Molecular Connectivity Index) approach of the KOCWIN v2.00 program followed by an determination of an overall weighted-average value using the mole fractions of all the individual components.

MCI based methodology:
PCKOCWIN (version 1) estimated Koc solely with a QSAR utilizing First Order Molecular Connectivity Index (MCI). This QSAR estimation methodology is described completely in a journal article (Meylan et al, 1992) and in a report prepared for the EPA (SRC, 1991). PCKOCWIN (version 2) utilizes the same methodology, but the QSAR has been re-regressed using a larger database of experimental Koc values that includes many new chemicals and structure types.
Reference: Meylan, W., P.H. Howard and R.S. Boethling, "Molecular Topology/Fragment Contribution Method for Predicting Soil Sorption Coefficients", Environ. Sci. Technol. 26: 1560-7 (1992).

Validity of model
1. Defined endpoint: log Koc – soil adsorption coefficient of organic compounds.
2. Unambiguous algorithm:
log Koc = 0.5213 MCI + 0.60 + ΣPfN
MCI – molecular connectivity index, ΣPfN - summation of the products of all applicable correction factor coefficients available in the data set multiplied by the number of times (N) that factor is counted for the structure.
3. Applicability domain: Currently, there is no universally accepted definition of model domain. The training set of the model contains diverse molecules, so that the fragment library is abundant. It is however possible that a compound has functional groups or other structural features that are not represented in the training set and for which no fragment coefficients were developed. Additionally, there can be more instances of a given fragment than the maximum for all training set compounds. These points should be taken into consideration while interpreting test results.
Molecular weight limits of the training set: 32-665 g/mol
Log Kow limits: -2.11-9.10
4. Appropriate measures of goodness of fit, robustness and predictivity: for the statistics, training data set has been split up into two subsets: the one containing non-polar substances with no fragments subjected to corrections (i.e. those with ΣPfN = 0) and the one containing the remaining ones. For the non-polar set: N = 69 compounds, correlation coefficient R2= 0.967, standard deviation sd = 0.247 and average deviation ad = 0.199. For the second set: N = 447 compounds, correlation coefficient R2= 0.9, standard deviation sd = 0.34 and average deviation ad = 0.273. For the external validation data set: N = 158 compounds, correlation coefficient R2= 0.85, standard deviation sd = 0.583 and average deviation ad = 0.459. For the 516 compounds in the training set, 93% are within 0.6 log units and 100% within 1 log unit. For the accuracry graphs, please refer to the PDF under 'attached background material'.
5. Mechanistic interpretation if possible: The methodology and relationship between the first order molecular connectivity index (MCI) and adsorption coefficient is outlined in the reference paper: Meylan, W., P.H. Howard and R.S. Boethling, "Molecular Topology/Fragment Contribution Method for Predicting Soil Sorption Coefficients", Environ. Sci. Technol. 26: 1560-7 (1992). MCI was initially successfully used to predict soil sorption coefficients for non-polar organics, and the developed new estimation method based on MCI and series of statistically derived fragment contribution factors made it useful also for the polar ones.

Key result
Type:
log Koc
Value:
ca. 6.029 dimensionless
Remarks on result:
other: weighted average estimation using MCI method of KOCWIN v.2.00

Details on results:

Chemical names SMILES Mole fraction Xi = (mi/Mi)/∑ (mi/Mi) log Koc log Koc * xi Domain evaulation
Fatty acids C16-18 and C18-unsatd. pentaerythritol diesters CCCCCCCCCCCCCCCC(=O)OCC(CO)(CO)COC(=O)CCCCCCCC=CCC=CCC=CCC 0.084963 6.85 0.582380035 ID (Molecular weight) OD (fragments)
Fatty acids C16-18 and C18-unsatd. Pentaerythritol triesters CCCCCCCCCCCCCCCC(=O)OCC(CO)(COC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 0.023379 10.00 0.233788573 OD (Molecular weight) ID (fragments)
Fatty acids C18 and C18-unsatd. pentaerythritol monoesters CCC=CCC=CCC=CCCCCCCCC(=O)OCC(CO)(CO)CO 0.075580 3.78 0.285365535 ID (Molecular weight) OD (fragments)
Fatty acids C18 and C18-unsatd. pentaerythritol diesters CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)(CO)COC(=O)CCCCCCCC=CCC=CCC=CCC 0.117890 7.38 0.869540608 ID (Molecular weight) OD (fragments)
Fatty acids C18 and C18-unsatd. pentaerythritol triesters CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)(COC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCC=CCC 0.097370 10.00 0.973698021 OD (Molecular weight) ID (fragments)
Fatty acids C16-18 and C18-unsatd. glycerol diesters CCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCC=CCC=CCC=CCC 0.095848 6.90 0.661662148 ID (Molecular weight and fragments)
Fatty acids C18 and C18-unsatd. glycerol monoesters CCC=CCC=CCC=CCCCCCC(=O)OCC(O)CO 0.277132 2.51 0.694631535 ID (Molecular weight) OD (fragments)
Fatty acids C18 and C18-unsatd. glycerol diesters CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COC(=O)CCCCCC=CCC=CCC=CCC 0.213756 7.42 1.58704499 ID (Molecular weight and fragments)
Fatty acids C18 and C18-unsatd. glycerol triesters CCCCCCCCC=CCCCCCCCC(=O)OCC(COC(=O)CCCCCC=CCC=CCC=CCC)OC(=O)CCCCCCCC=CCC=CCCCCC 0.014082 10.00 0.14082267 OD (Molecular weight) ID (fragments)
        6.028934115  

ID = in domain; OD = out of doamin

Koc
SMILES : CCCCCCCCCCCCCCCC(=O)OCC(CO)(CO)COC(=O)CCCCCCCC=CCC=CCC=CCC      
CHEM  :       
MOL FOR: C39 H70 O6  Domain evaluation MW (Training set)  
MOL WT : 634.99 ID 665.02  
--------------------------- KOCWIN v2.00 Results ---------------------------      
       
 Koc Estimate from MCI:      
 ---------------------      
        First Order Molecular Connectivity Index ........... : 22.030      
        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 12.0842      
        Fragment Correction(s):   Training set  
                 2  Aliphatic Alcohol (-C-OH) ........... : -2.6358 OD 1  
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -2.5939 ID 2  
        Corrected Log Koc .................................. : 6.8545      
       
                        Estimated Koc: 7.153e+006 L/kg  <===========      
       
 Koc Estimate from Log Kow:      
 -------------------------      
        Log Kow (Kowwin estimate) ......................... : 13.33      
        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 8.2983      
        Fragment Correction(s):      
                 2  Aliphatic Alcohol (-C-OH) ........... : -0.8229      
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312      
        Corrected Log Koc .................................. : 7.3442      
       
                        Estimated Koc: 2.209e+007 L/kg  <===========      
       
       
SMILES : CCCCCCCCCCCCCCCC(=O)OCC(CO)(COC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCC      
        C=CCC=CCC=CCC      
CHEM  :       
MOL FOR: C57 H100 O7  Domain evaluation MW (Training set)  
MOL WT : 897.43 OD 665.02  
--------------------------- KOCWIN v2.00 Results ---------------------------      
       
 Koc Estimate from MCI:      
 ---------------------      
        First Order Molecular Connectivity Index ........... : 31.424      
        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 16.9812      
        Fragment Correction(s):   Training set  
                 1  Aliphatic Alcohol (-C-OH) ........... : -1.3179 ID 1  
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -2.5939 ID 2  
        Corrected Log Koc .................................. : 13.0694      
       
                        Estimated Koc: 1e+010 L/kg  <===========      
       
 Koc Estimate from Log Kow:      
 -------------------------      
        Log Kow (Kowwin estimate) ......................... : 21.36      
        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 12.7400      
        Fragment Correction(s):      
                 1  Aliphatic Alcohol (-C-OH) ........... : -0.4114      
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312      
        Corrected Log Koc .................................. : 12.1973      
       
                        Estimated Koc: 1.575e+012 L/kg  <===========      
       
       
SMILES : CCC=CCC=CCC=CCCCCCCCC(=O)OCC(CO)(CO)CO      
CHEM  :       
MOL FOR: C23 H40 O5  Domain evaluation MW (Training set)  
MOL WT : 396.57 ID 665.02  
--------------------------- KOCWIN v2.00 Results ---------------------------      
       
 Koc Estimate from MCI:      
 ---------------------      
        First Order Molecular Connectivity Index ........... : 13.636      
        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 7.7085      
        Fragment Correction(s):   Training set  
                 2  Aliphatic Alcohol (-C-OH) ........... : -2.6358 OD 1  
                 1  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -1.2970 ID 2  
        Corrected Log Koc .................................. : 3.7757      
       
                        Estimated Koc: 5966 L/kg  <===========      
       
 Koc Estimate from Log Kow:      
 -------------------------      
        Log Kow (Kowwin estimate) ......................... : 6.45      
        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 4.4928      
        Fragment Correction(s):      
                 2  Aliphatic Alcohol (-C-OH) ........... : -0.8229      
                 1  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.0656      
        Corrected Log Koc .................................. : 3.6043      
       
                        Estimated Koc: 4021 L/kg  <===========      
       
       
SMILES : CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)(CO)COC(=O)CCCCCCCC=CCC=CCC=CCC      
CHEM  :       
MOL FOR: C41 H72 O6  Domain evaluation MW (Training set)  
MOL WT : 661.03 ID 665.02  
--------------------------- KOCWIN v2.00 Results ---------------------------      
       
 Koc Estimate from MCI:      
 ---------------------      
        First Order Molecular Connectivity Index ........... : 23.030      
        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 12.6055      
        Fragment Correction(s):   Training set  
                 2  Aliphatic Alcohol (-C-OH) ........... : -2.6358 OD 1  
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -2.5939 ID 2  
        Corrected Log Koc .................................. : 7.3758      
       
                        Estimated Koc: 2.376e+007 L/kg  <===========      
       
 Koc Estimate from Log Kow:      
 -------------------------      
        Log Kow (Kowwin estimate) ......................... : 14.10      
        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 8.7242      
        Fragment Correction(s):      
                 2  Aliphatic Alcohol (-C-OH) ........... : -0.8229      
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312      
        Corrected Log Koc .................................. : 7.7702      
       
                        Estimated Koc: 5.891e+007 L/kg  <===========      
       
       
SMILES : CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)(COC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCC      
        CCCC=CCC=CCC=CCC      
CHEM  :       
MOL FOR: C59 H102 O7  Domain evaluation MW (Training set)  
MOL WT : 923.47 OD 665.02  
--------------------------- KOCWIN v2.00 Results ---------------------------      
       
 Koc Estimate from MCI:      
 ---------------------      
        First Order Molecular Connectivity Index ........... : 32.424      
        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 17.5025      
        Fragment Correction(s):   Training set  
                 1  Aliphatic Alcohol (-C-OH) ........... : -1.3179 ID 1  
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -2.5939 ID 2  
        Corrected Log Koc .................................. : 13.5907      
       
                        Estimated Koc: 1e+010 L/kg  <===========      
       
 Koc Estimate from Log Kow:      
 -------------------------      
        Log Kow (Kowwin estimate) ......................... : 22.13      
        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 13.1659      
        Fragment Correction(s):      
                 1  Aliphatic Alcohol (-C-OH) ........... : -0.4114      
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312      
        Corrected Log Koc .................................. : 12.6232      
       
                        Estimated Koc: 4.2e+012 L/kg  <===========      
       
       
SMILES : CCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCC=CCC=CCC=CCC      
CHEM  :       
MOL FOR: C35 H62 O5  Domain evaluation MW (Training set)  
MOL WT : 562.88 ID 665.02  
--------------------------- KOCWIN v2.00 Results ---------------------------      
       
 Koc Estimate from MCI:      
 ---------------------      
        First Order Molecular Connectivity Index ........... : 19.596      
        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 10.8151      
        Fragment Correction(s):   Training set  
                 1  Aliphatic Alcohol (-C-OH) ........... : -1.3179 ID 1  
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -2.5939 ID 2  
        Corrected Log Koc .................................. : 6.9032      
       
                        Estimated Koc: 8.003e+006 L/kg  <===========      
       
 Koc Estimate from Log Kow:      
 -------------------------      
        Log Kow (Kowwin estimate) ......................... : 12.46      
        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 7.8171      
        Fragment Correction(s):      
                 1  Aliphatic Alcohol (-C-OH) ........... : -0.4114      
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312      
        Corrected Log Koc .................................. : 7.2745      
       
                        Estimated Koc: 1.881e+007 L/kg  <===========      
       
       
SMILES : CCC=CCC=CCC=CCCCCCC(=O)OCC(O)CO      
CHEM  :       
MOL FOR: C19 H32 O4  Domain evaluation MW (Training set)  
MOL WT : 324.46 ID 665.02  
--------------------------- KOCWIN v2.00 Results ---------------------------      
       
 Koc Estimate from MCI:      
 ---------------------      
        First Order Molecular Connectivity Index ........... : 11.202      
        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 6.4394      
        Fragment Correction(s):   Training set  
                 2  Aliphatic Alcohol (-C-OH) ........... : -2.6358 OD 1  
                 1  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -1.2970 ID 2  
        Corrected Log Koc .................................. : 2.5066      
       
                        Estimated Koc: 321 L/kg  <===========      
       
 Koc Estimate from Log Kow:      
 -------------------------      
        Log Kow (Kowwin estimate) ......................... : 4.99      
        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 3.6852      
        Fragment Correction(s):      
                 2  Aliphatic Alcohol (-C-OH) ........... : -0.8229      
                 1  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.0656      
        Corrected Log Koc .................................. : 2.7967      
       
                        Estimated Koc: 626.2 L/kg  <===========      
       
       
SMILES : CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COC(=O)CCCCCC=CCC=CCC=CCC      
CHEM  :       
MOL FOR: C37 H64 O5  Domain evaluation MW (Training set)  
MOL WT : 588.92 ID 665.02  
--------------------------- KOCWIN v2.00 Results ---------------------------      
       
 Koc Estimate from MCI:      
 ---------------------      
        First Order Molecular Connectivity Index ........... : 20.596      
        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 11.3364      
        Fragment Correction(s):   Training set  
                 1  Aliphatic Alcohol (-C-OH) ........... : -1.3179 ID 1  
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -2.5939 ID 2  
        Corrected Log Koc .................................. : 7.4245      
       
                        Estimated Koc: 2.658e+007 L/kg  <===========      
       
 Koc Estimate from Log Kow:      
 -------------------------      
        Log Kow (Kowwin estimate) ......................... : 13.23      
        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 8.2430      
        Fragment Correction(s):      
                 1  Aliphatic Alcohol (-C-OH) ........... : -0.4114      
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312      
        Corrected Log Koc .................................. : 7.7004      
       
                        Estimated Koc: 5.016e+007 L/kg  <===========      
       
       
SMILES : CCCCCCCCC=CCCCCCCCC(=O)OCC(COC(=O)CCCCCC=CCC=CCC=CCC)OC(=O)CCCCCCCC=C      
        CC=CCCCCC      
CHEM  :       
MOL FOR: C55 H94 O6  Domain evaluation MW (Training set)  
MOL WT : 851.36 OD 665.02  
--------------------------- KOCWIN v2.00 Results ---------------------------      
       
 Koc Estimate from MCI:      
 ---------------------      
        First Order Molecular Connectivity Index ........... : 30.028      
        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 16.2532      
        Fragment Correction(s):   Training set  
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -2.5939 ID 2  
        Corrected Log Koc .................................. : 13.6593      
       
                        Estimated Koc: 1e+010 L/kg  <===========      
       
 Koc Estimate from Log Kow:      
 -------------------------      
        Log Kow (Kowwin estimate) ......................... : 21.66      
        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 12.9059      
        Fragment Correction(s):      
                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312      
        Corrected Log Koc .................................. : 12.7747      
       
                        Estimated Koc: 5.953e+012 L/kg  <===========      
Validity criteria fulfilled:
not applicable
Conclusions:
Using the MCI (Molecular Connectivity Index) approach of the KOCWIN v2.00 program (EPI Suite v4.11), the weighted average log Koc of the test substance wasre calculated to be 6.0289
Executive summary:

The soil adsorption coefficient (Koc) of the test substance was estimated using the MCI (Molecular Connectivity Index) approach of the KOCWIN v2.00 program (EPI Suite v4.11). Since the test substance is a UVCB with similar constituents varying mainly in carbon chain lengths, the Koc values were estimated for the individual components followed by the determination of an overall weighted-average value using the mole fractions of all the individual components. SMILES codes were used as input parameters. The estimated log Koc of the individual constituents ranged from 2.51 to 10 and the weighted average log was 6.0289 (US EPA, 2017). This range of Koc indicates strong sorption potential to soil/sediment and negligible to slow migration to ground water. The estimates for the major constituents are considered to be reliable with restrictions, as they do not completely fall within of the applicability domain.

Description of key information

Key value for chemical safety assessment

Koc at 20 °C:
6.029

Additional information

The soil adsorption coefficient (Koc) of the test substance was estimated using the MCI (Molecular Connectivity Index) approach of the KOCWIN v2.00 program (EPI Suite v4.11). Since the test substance is a UVCB with similar constituents varying mainly in carbon chain lengths, the Koc values were estimated for the individual components followed by the determination of an overall weighted-average value using the mole fractions of all the individual components. SMILES codes were used as input parameters. The estimated log Koc of the individual constituents ranged from 2.51 to 10 and the weighted average log was 6.0289 (US EPA, 2017). This range of Koc indicates strong sorption potential to soil/sediment and negligible to slow migration to ground water. The estimates for the major constituents are considered to be reliable with restrictions, as they do not completely fall within of the applicability domain.