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Reference
Endpoint:
adsorption / desorption
Remarks:
adsorption
Type of information:
calculation (if not (Q)SAR)
Adequacy of study:
weight of evidence
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
accepted calculation method
Justification for type of information:
Estimated data generated using the EPI Suite model developed by the USEPA.
Reference:
Composition 1
Qualifier:
according to
Guideline:
other: Modeling database
Principles of method if other than guideline:
Prediction done using KOCWIN Program (v2.00)
GLP compliance:
not specified
Type of method:
other: MCI Method
Media:
soil
Test material information:
Composition 1
Specific details on test material used for the study:
- Name of test material: 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione
- Molecular formula: C26H30N2O2
- Molecular weight: 402.535 g/mol
- Smiles notation: O=C1c2c(c(NC3CCCCC3)ccc2)C(=O)c2cccc(NC3CCCCC3)c12
- InChl: 1S/C26H30N2O2/c29-25-20-14-8-16-22(28-18-11-5-2-6-12-18)24(20)26(30)19-13-7-15-21(23(19)25)27-17-9-3-1-4-10-17/h7-8,13-18,27-28H,1-6,9-12H2
- Substance type: Organic
- Physical state: Solid
Radiolabelling:
not specified
Test temperature:
25 deg.C
Analytical monitoring:
not specified
Key result
Type:
Koc
Value:
35 140 L/kg
Temp.:
25 °C
Remarks on result:
other: Log Koc=4.5458 (estimated by MCI method)
Transformation products:
not specified

KOCWIN Program (v2.00) Results:

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

SMILES : O=C(c(c(c(NC(CCCC1)C1)cc2)C(=O)c3cccc4NC(CCCC5)C5)c2)c34

CHEM : 9,10-Anthracenedione, 1,5-bis(cyclohexylamino)-

MOL FOR: C26 H30 N2 O2

MOL WT : 402.54

--------------------------- KOCWIN v2.00 Results ---------------------------

Koc Estimate from MCI:

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

First Order Molecular Connectivity Index ........... : 14.720

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 8.2735

Fragment Correction(s):

2 Nitrogen to non-fused aromatic ring ... : -1.0450

2 Nitrogen-to-Cycloalkane (aliphatic) ... : -1.7232

2 Ketone (-C-CO-C-) ................... : -2.2581

* Quinone (diketone) ring ............... : 1.2986

Corrected Log Koc .................................. : 4.5458

Estimated Koc: 3.514e+004 L/kg <===========

Validity criteria fulfilled:
not specified
Conclusions:
The soil adsorption coefficient i.e Koc value of 1,5 -bis(cyclohexylamino)-9,10 -dihydroanthracene -9,10 -dione was estimated to be 35140.0 L/kg (log Koc= 4.5458)  by means of MCI method (at 25 deg C). This Koc value indicates that the substance 1,5 -bis(cyclohexyl amino)-9,10 -dihydroanthracene-9,10 -dione has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.
Executive summary:

KOCWIN model (v2.00) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the soil adsorption coefficient i.e Koc value of test chemical 1,5 -bis(cyclo hexylamino)-9,10 -dihydroanthracene-9,10 -dione (CAS No. 15958 -68 -6). The soil adsorption coefficient i.e Koc value of 1,5 -bis(cyclohexylamino)-9,10 -dihydroanthracene -9,10 -dione was estimated to be 35140.0 L/kg (log Koc= 4.5458)  by means of MCI method (at 25 deg C). This Koc value indicates that the substance 1,5 -bis(cyclohexyl amino)-9,10 -dihydroanthracene-9,10 -dione has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

Description of key information

KOCWIN model (v2.00) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the soil adsorption coefficient i.e Koc value of test chemical 1,5 -bis(cyclo hexylamino)-9,10 -dihydroanthracene-9,10 -dione (CAS No. 15958 -68 -6). The soil adsorption coefficient i.e Koc value of 1,5 -bis(cyclohexylamino)-9,10 -dihydroanthracene -9,10 -dione was estimated to be 35140.0 L/kg (log Koc= 4.5458)  by means of MCI method (at 25 deg C). This Koc value indicates that the substance 1,5 -bis(cyclohexyl amino)-9,10 -dihydroanthracene-9,10 -dione has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

Key value for chemical safety assessment

Koc at 20 °C:
35 140
Log Koc at 20 °C:
4.546

Additional information

Various predicted data for the target compound1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(CAS No. 15958-68-6) and supporting weight of evidence study for its read across substance were reviewed for the adsorption end point which are summarized as below:

 

In aprediction done using theKOCWIN Program(v2.00) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the soil adsorption coefficient i.e Koc value of test chemical 1,5 -bis(cyclo hexylamino)-9,10 -dihydroanthracene-9,10 -dione (CAS No. 15958 -68 -6). The soil adsorption coefficient i.e Koc value of 1,5 -bis(cyclohexylamino)-9,10 -dihydroanthracene -9,10 -dione was estimated to be 35140.0 L/kg (log Koc= 4.5458)  by means of MCI method (at 25 deg C).

 

The Soil Adsorption Coefficient i.e Koc value of test substance 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione (CAS no. 15958 -68 -6) was estimated using Adsorption Coefficient module (v12.1.0.50374) program as Koc 23.8 , 190, 5695, 36344, 56816, 60027, 60366, 60400 and 60404 at pH range 0, 1, 2, 3, 4, 5, 6, 7 and 8 -14 respectively (log Koc value range from1.4 ± 1.0 to 4.8 ± 1.0)(ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017).

 

In an another prediction done by using ChemSpider Database (2017),the Soil Adsorption Coefficient i.e Koc value of test substance 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione (CAS no. 15958 -68 -6) was estimated. The adsorption coefficient (Koc) value of substance 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione was estimated to be 37011.89 (Log Koc = 4.568) at pH 5.5 and 37084.46 (Log Koc = 4.569) at pH 7.4, respectively.

 

Additional soil adsorption coefficient i.e Koc value of test chemical1,5 -bis(cyclohexyl amino)-9,10 -dihydroanthracene-9,10 -dione (CAS No. 15958 -68 -6)was estimated using the SciFinder database (American Chemical Society (ACS), 2017).The soil adsorption coefficient i.e Koc value of 1,5 -bis(cyclohexylamino)-9,10 -dihydroanthracene-9,10 -dione was estimated to be 449, 13500, 85900, 134000, 142000 and 143000 at pH range 1, 2, 3, 4, 5 and 6 -10, respectively (log Koc value ranges from 2.652 to 5.15) (at 25 deg C).

 

From CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application)  V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical), the adsorption coefficient i.e KOC for test substance 1,5 -bis(cyclohexylamino)-9,10 -dihydro anthracene-9,10 -dione (CAS no. 15958 -68 -6) was estimated to be 119000 L/kg (log Koc = 5.07).The predicted KOC result based on the 5 OECD principles.

 

In a supporting weight of evidence study from authoritative database (HSDB, 2017) for the read across chemical 1,4-Bis(p-tolylamino)anthraquinone (CAS no.128-80-3), adsorption experiment was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 1,4-Bis(p-tolylamino)anthraquinone. The adsorption coefficient (Koc) value was calculated using a structure estimation method based on molecular connectivity indices. The adsorption coefficient (Koc) value of substance 1,4 -Bis(p-tolylamino)anthraquinone was estimated to be 4800000 (Log Koc = 6.681). This Koc value indicates that the substance 1,4 -Bis(p-tolylamino)anthraquinone has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

 

On the basis of above overall results for target chemical1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(from EPI suite, ACD labs,ChemSpider, SciFinder database and CompTox Chemistry Dashboard,2017) and for its read across substance (from authoritative database HSDB, 2017), it can be concluded that the Koc value of test substance1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione ranges from 23.8 –143000indicating that the test chemical 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dionehas a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.