4'-cyanoacetophenone

Toxicity to microorganisms

Link to relevant study record(s)

Reference

Endpoint:

toxicity to microorganisms

Type of information:

(Q)SAR

Adequacy of study:

weight of evidence

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 limited documentation / justification

Justification for type of information:

Data is from OECD QSAT toolbox version 3.3 and the QMRF report has been attached.

Qualifier:

according to guideline

Guideline:

other: Estimated data

Principles of method if other than guideline:

Prediction was done using the OECD QSAR toolbox version .3.

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material : 4'-Cyanoacetophenone
- Molecular formula : C9H7NO
- Molecular weight : 145.16 g/mol
- Smiles notation : CC(=O)c1ccc(C#N)cc1
- InChl : 1S/C9H7NO/c1-7(11)9-4-2-8(6-10)3-5-9/h2-5H,1H3
- Substance type: Organic
- Physical state: Solid

Analytical monitoring:

not specified

Vehicle:

not specified

Test organisms (species):

Tetrahymena pyriformis

Test type:

static

Water media type:

freshwater

Total exposure duration:

48 h

Test temperature:

20-22°C

pH:

7.6 - 7.7

Nominal and measured concentrations:

Estimated data

Reference substance (positive control):

not specified

Key result

Duration:

48 h

Dose descriptor:

other: IGC50

Effect conc.:

555.036 mg/L

Nominal / measured:

estimated

Conc. based on:

not specified

Basis for effect:

other: Growth

Remarks on result:

other: Other details not known

The prediction was based on dataset comprised from the following descriptors: IGC50
Estimation method: Takes average value from the 8 nearest neighbours
Domain  logical expression:Result: In Domain

((((((((("a" or "b" or "c" or "d" )  and ("e" and ( not "f") )  )  and ("g" and ( not "h") )  )  and ("i" and ( not "j") )  )  and ("k" and ( not "l") )  )  and "m" )  and ("n" and ( not "o") )  )  and "p" )  and ("q" and "r" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Aromatic compound OR Carbonyl compound OR Ketone OR Nitrile by Organic functional groups, Norbert Haider (checkmol) ONLY

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Acetylenic Carbon [#C] OR Aliphatic Carbon [CH] OR Aliphatic Carbon [-CH2-] OR Aliphatic Carbon [-CH3] OR Aromatic Carbon [C] OR Carbonyl, aliphatic attach [-C(=O)-] OR Carbonyl, olefinic attach [-C(=O)-] OR Carbonyl, one aromatic attach [-C(=O)-] OR Cyano, aromatic attach [-C#N] OR Miscellaneous sulfide (=S) or oxide (=O) OR Olefinic carbon [=CH- or =C<] by Organic functional groups (US EPA) ONLY

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Aryl OR Ketone OR Nitrile OR Overlapping groups by Organic Functional groups (nested) ONLY

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Aryl OR Ketone OR Nitrile by Organic Functional groups ONLY

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OASIS v.1.3

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >>  Michael-type addition, quinoid structures OR AN2 >>  Michael-type addition, quinoid structures >> Quinones OR AN2 >> Nucleophilic addition to alpha, beta-unsaturated carbonyl compounds OR AN2 >> Nucleophilic addition to alpha, beta-unsaturated carbonyl compounds >> alpha, beta-Unsaturated Aldehydes OR AN2 >> Schiff base formation OR AN2 >> Schiff base formation >> alpha, beta-Unsaturated Aldehydes OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Acridone, Thioxanthone, Xanthone and Phenazine Derivatives OR Non-covalent interaction >> DNA intercalation >> Aminoacridine DNA Intercalators OR Non-covalent interaction >> DNA intercalation >> Fused-Ring Primary Aromatic Amines OR Non-covalent interaction >> DNA intercalation >> Quinones OR Radical OR Radical >> Radical mechanism by ROS formation OR Radical >> Radical mechanism by ROS formation >> Acridone, Thioxanthone, Xanthone and Phenazine Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Fused-Ring Primary Aromatic Amines OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones OR SN1 OR SN1 >> Alkylation after metabolically formed carbenium ion species OR SN1 >> Alkylation after metabolically formed carbenium ion species >> Polycyclic Aromatic Hydrocarbon Derivatives OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Fused-Ring Primary Aromatic Amines OR SN2 OR SN2 >> Alkylation, direct acting epoxides and related after P450-mediated metabolic activation OR SN2 >> Alkylation, direct acting epoxides and related after P450-mediated metabolic activation >> Polycyclic Aromatic Hydrocarbon Derivatives OR SN2 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Quinoline Derivatives OR SN2 >> SN2 at an activated carbon atom OR SN2 >> SN2 at an activated carbon atom >> Quinoline Derivatives by DNA binding by OASIS v.1.3

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OECD

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Michael addition OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Arenes OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Polycyclic (PAHs) and heterocyclic (HACs) aromatic hydrocarbons-Michael addition OR Michael addition >> Polarised Alkenes-Michael addition OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated ketones OR Schiff base formers OR Schiff base formers >> Direct Acting Schiff Base Formers OR Schiff base formers >> Direct Acting Schiff Base Formers >> Alpha-beta-dicarbonyl OR SN1 OR SN1 >> Carbenium Ion Formation OR SN1 >> Carbenium Ion Formation >> Polycyclic (PAHs) and heterocyclic (HACs) aromatic hydrocarbons-SN1 OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Aromatic nitro OR SN1 >> Nitrenium Ion formation >> Primary aromatic amine OR SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine by DNA binding by OECD

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Non binder, without OH or NH2 group by Estrogen Receptor Binding

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Non binder, non cyclic structure by Estrogen Receptor Binding

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as No alert found by Protein binding by OASIS v1.3

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Michael Addition OR Michael Addition >> Michael addition on conjugated systems with electron withdrawing group OR Michael Addition >> Michael addition on conjugated systems with electron withdrawing group >> alpha,beta-Carbonyl compounds with polarized triple bond  OR Michael Addition >> Polarised Alkenes OR Michael Addition >> Polarised Alkenes >> Polarised Alkene - alkenyl pyridines, pyrazines, pyrimidines or triazines  OR Schiff base formation OR Schiff base formation >> Schiff base formation with carbonyl compounds OR Schiff base formation >> Schiff base formation with carbonyl compounds >> Aldehydes OR SN2 OR SN2 >> Nucleophilic substitution on benzilyc carbon atom OR SN2 >> Nucleophilic substitution on benzilyc carbon atom >> alpha-Activated benzyls  by Protein binding by OASIS v1.3

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Class 5 (Not possible to classify according to these rules) by Acute aquatic toxicity classification by Verhaar (Modified) ONLY

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Aromatic-H AND Cyanide / Nitriles   [-C#N] AND Ketone   [-C-C(=O)-C-] AND Methyl  [-CH3] by Biodegradation fragments (BioWIN MITI)

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as Aromatic-CH OR Aromatic-CH3 OR -CH2-  [linear] OR Pyridine ring by Biodegradation fragments (BioWIN MITI)

Domain logical expression index: "p"

Similarity boundary:Target: CC(=O)c1ccc(C#N)cc1
Threshold=30%,
Dice(Atom centered fragments)
Atom type; Count H attached; Hybridization

Domain logical expression index: "q"

Parametric boundary:The target chemical should have a value of log Kow which is >= -0.0632

Domain logical expression index: "r"

Parametric boundary:The target chemical should have a value of log Kow which is <= 3.15

Validity criteria fulfilled:

not specified

Conclusions:

The IGC50 value was estimated to be 555.035 mg/l when 4'-Cyanoacetophenone exposed to Tetrahymena pyriformis for 48hrs.  
 

Executive summary:

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the eight closest read across substances, toxicity on Tetrahymena pyriformis was predicted for 4'-Cyanoacetophenone (1443-80-7). The IGC50 value was estimated to be 555.035 mg/l when 4'-Cyanoacetophenone exposed to Tetrahymena pyriformis for 48hrs.  

 

Description of key information

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the eight closest read across substances, toxicity on Tetrahymena pyriformis was predicted for 4'-Cyanoacetophenone (1443-80-7). The IGC50 value was estimated to be 555.035 mg/l when 4'-Cyanoacetophenone exposed to Tetrahymena pyriformis for 48hrs.  

 

Key value for chemical safety assessment

EC50 for microorganisms:

555.035 mg/L

Additional information

Based on the various predicted data and experimental data for target chemical 4'-Cyanoacetophenone (1443-80-7) and experimental data for read across chemical studyhave been reviewed to determine the toxic nature of target chemical 4'-Cyanoacetophenone the studies are as mentioned below:

 

In the first predicted weight of evidence report for the 4'-Cyanoacetophenone (1443-80-7) from SSS (QSAR, 2017) toxicity study was carried out. Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the eight closest read across substances, toxicity on Tetrahymena pyriformis was predicted for 4'-Cyanoacetophenone (1443-80-7). The IGC50 value was estimated to be 555.035 mg/l when 4'-Cyanoacetophenone exposed to Tetrahymena pyriformis for 48hrs.   

 

Similarly in the second weight of evidence study for the 4'-Cyanoacetophenone (1443-80-7) from Water Pollution Research Journal of Canada, 1991. The comparatively quick and low cost bioassay with Photobacterium phosphoreum, strain NRRL-B-11177 (Microtox3), occasionally also referred to as Vibrio fischerii, strain NRRL-B-11177 was used to assess the toxicity of 4 acetylbenzonitrile to aquatic bacteria. The luminescent bacterial bioassay requires only a short period of time, i.e. minutes. In terms of testing a broad range of different chemicals with many different modes of action, a somewhat longer assay time, i.e. 30 min, is preferred, mainly to ascertain that potential diffusion problems are eliminated at source. Normally the pT values for a particular chemical rarely vary much with exposure time. The most commonly used operating conditions are 15°C for the EC50tests with exposure times of 5 to 30 min. The pH of the test system can vary in the range of 5< pH <9 without great effect on the luminescence. The Effective Concentration causing 50% mortality of luminescent bacteria Photobacterium phosphereum was determine to be 51.5mg/l after 30 minutes exposure to 4 acetylbenzonitrile. Antibacterial activity of 3-Methoxyacetophenone was observed for microorganism determined by minimum inhibitory concentration using by two-fold dilution method. Hydrophobicity was observed for the bacteria more hydrophobic the bacterial cell, the greater is its affinity to the hydrocarbon, resulting in a transfer of cells from the aqueous suspension to the organic phase, leading to a reduction in the turbidity of the culture in the former. Optical density (OD) was measured at concentrations from 0.0 to 0.2ml. Bacteria were cultured in medium at mid-logarithmic phase and followed the protocol. OD was measured at 400 nm and cell-free buffer served as the blank.A plot was made between OD and different hexadecane concentrations. After experiment it was determined that the Minimum Inhibitory Concentration (MIC) of Bacillus subtilis NCIM 2718 and Salmonella typhi NCIM2501 for 3-Methoxyacetophenone (586-37-8) was determined as 0.0629 mg/l.

 

 

Similarly in the third weight of evidence study for the read across chemical (586-37-8) (From Chemical Biology & Drug Design, 2008). Antibacterial activity of 3-Methoxyacetophenonewas observed for microorganism determined by minimum inhibitory concentration using by two-fold dilution method. Hydrophobicity was observed for the bacteria more hydrophobic the bacterial cell, the greater is its affinity to the hydrocarbon, resulting in a transfer of cells from the aqueous suspension to the organic phase, leading to a reduction in the turbidity of the culture in the former. Optical density (OD) was measured at concentrations from 0.0 to 0.2ml. Bacteria were cultured in medium at mid-logarithmic phase and followed the protocol. OD was measured at 400 nm and cell-free buffer served as the blank. A plot was made between OD and different hexadecane concentrations. After experiment it was determined that the Minimum Inhibitory Concentration (MIC) of Bacillus subtilis NCIM 2718 and Salmonella typhi NCIM2501 for 3-Methoxyacetophenone (586-37-8) was determined as 0.0629 mg/l.