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Short-term toxicity to aquatic invertebrates

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Reference
Endpoint:
short-term toxicity to aquatic invertebrates
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 QSAR toolbox version.3.3 and QMRF report has been attached.
Qualifier:
according to guideline
Guideline:
other: Predicted data
Principles of method if other than guideline:
Prediction is done using QSAR Toolbox version 3.3 with log kow as the primary discriptors.
GLP compliance:
not specified
Specific details on test material used for the study:
- Name of test material (IUPAC name): Cinnamyl formate
- Common name: 3-Phenylallyl formate
- Molecular formula: C10H10O2
- Molecular weight: 162.187 g/mol
- Smiles notation: c1(\C=C\COC=O)ccccc1
- InChl: 1S/C10H10O2/c11-9-12-8-4-7-10-5-2-1-3-6-10/h1-7,9H,8H2/b7-4+
- Substance type: Organic
-physical state: liquid
Analytical monitoring:
not specified
Vehicle:
not specified
Test organisms (species):
Daphnia magna
Test type:
static
Water media type:
freshwater
Limit test:
no
Total exposure duration:
2 d
Key result
Duration:
48 h
Dose descriptor:
EC50
Effect conc.:
148.28 mg/L
Nominal / measured:
estimated
Conc. based on:
test mat.
Basis for effect:
mobility
Remarks on result:
other: not toxic

The prediction was based on dataset comprised from the following descriptors: EC50
Estimation method: Takes average value from the 6 nearest neighbours
Domain  logical expression:Result: In Domain

((((((((((((((((((("a" or "b" or "c" )  and ("d" and ( not "e") )  )  and ("f" and ( not "g") )  )  and ("h" and ( not "i") )  )  and "j" )  and ("k" and ( not "l") )  )  and ("m" and ( not "n") )  )  and ("o" and ( not "p") )  )  and ("q" and ( not "r") )  )  and ("s" and ( not "t") )  )  and ("u" and ( not "v") )  )  and ("w" and ( not "x") )  )  and "y" )  and ("z" and ( not "aa") )  )  and ("ab" and ( not "ac") )  )  and ("ad" and ( not "ae") )  )  and ("af" and ( not "ag") )  )  and ("ah" and ( not "ai") )  )  and ("aj" and "ak" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Formic acid and formates by OECD HPV Chemical Categories

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Class 3 (unspecific reactivity) by Acute aquatic toxicity classification by Verhaar (Modified)

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Esters by Acute aquatic toxicity MOA by OASIS

Domain logical expression index: "d"

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

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> Direct Addition of an Acyl Halide OR Acylation >> Direct Addition of an Acyl Halide >> Acyl halide OR Acylation >> Isocyanates and Isothiocyanates OR Acylation >> Isocyanates and Isothiocyanates >> Isocyanates OR Acylation >> Isocyanates and Isothiocyanates >> Isothiocyanates OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates >> Formamides OR Michael addition OR Michael addition >> P450 Mediated Activation of Heterocyclic Ring Systems OR Michael addition >> P450 Mediated Activation of Heterocyclic Ring Systems >> Furans OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> 5-alkoxyindoles OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Alkyl phenols 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 >> Hydroquinones OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Methylenedioxyphenyl OR Michael addition >> Polarised Alkenes-Michael addition OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated aldehydes OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated amides OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated esters 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 >> Mono aldehydes OR SN1 OR SN1 >> Carbenium Ion Formation OR SN1 >> Carbenium Ion Formation >> Allyl benzenes OR SN1 >> Carbenium Ion Formation >> Alpha halo ethers (including alpha halo thioethers) OR SN1 >> Carbenium Ion Formation >> Hydrazine OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Aromatic azo OR SN1 >> Nitrenium Ion formation >> Aromatic nitro OR SN1 >> Nitrenium Ion formation >> Primary (unsaturated) heterocyclic amine OR SN1 >> Nitrenium Ion formation >> Primary aromatic amine OR SN1 >> Nitrenium Ion formation >> Secondary aromatic amine OR SN1 >> Nitrenium Ion formation >> Tertiary (unsaturated) heterocyclic amine  OR SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine OR SN1 >> Nitrenium Ion formation >> Unsaturated heterocyclic azo OR SN2 OR SN2 >> Direct Acting Epoxides and related OR SN2 >> Direct Acting Epoxides and related >> Epoxides OR SN2 >> Episulfonium Ion Formation OR SN2 >> Episulfonium Ion Formation >> 1,2-Dihaloalkanes OR SN2 >> Episulfonium Ion Formation >> Mustards OR SN2 >> P450 Mediated Epoxidation OR SN2 >> P450 Mediated Epoxidation >> Coumarins OR SN2 >> SN2 at an sp3 Carbon atom OR SN2 >> SN2 at an sp3 Carbon atom >> Aliphatic halides OR SN2 >> SN2 at an sp3 Carbon atom >> Sulfates by DNA binding by OECD

Domain logical expression index: "f"

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

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >>  Michael-type addition, quinoid structures OR AN2 >>  Michael-type addition, quinoid structures >> Quinoneimines OR AN2 >> Michael-type addition on alpha, beta-unsaturated carbonyl compounds OR AN2 >> Michael-type addition on alpha, beta-unsaturated carbonyl compounds >> Four- and Five-Membered Lactones 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 AN2 >> Schiff base formation >> Polarized Haloalkene Derivatives OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation >> Geminal Polyhaloalkane Derivatives OR AN2 >> Shiff base formation after aldehyde release OR AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters OR AN2 >> Shiff base formation for aldehydes OR AN2 >> Shiff base formation for aldehydes >> Geminal Polyhaloalkane Derivatives OR AN2 >> Shiff base formation for aldehydes >> Haloalkane Derivatives with Labile Halogen OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation >> Haloalkenes with Electron-Withdrawing Groups OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation >> Polarized Haloalkene Derivatives OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide Side Chain OR Radical OR Radical >> Generation of reactive oxygen species OR Radical >> Generation of reactive oxygen species >> Thiols OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Geminal Polyhaloalkane Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Single-Ring Substituted Primary Aromatic Amines OR Radical >> ROS formation after GSH depletion (indirect) OR Radical >> ROS formation after GSH depletion (indirect) >> Quinoneimines OR SN1 OR SN1 >> Carbenium ion formation OR SN1 >> Carbenium ion formation >> Alpha-Haloethers OR SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> Specific Acetate Esters OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Single-Ring Substituted Primary Aromatic Amines OR SN2 OR SN2 >> Acylation OR SN2 >> Acylation >> Specific Acetate Esters OR SN2 >> Acylation involving a leaving group  OR SN2 >> Acylation involving a leaving group  >> Geminal Polyhaloalkane Derivatives OR SN2 >> Acylation involving a leaving group  >> Haloalkane Derivatives with Labile Halogen OR SN2 >> Acylation involving a leaving group after metabolic activation OR SN2 >> Acylation involving a leaving group after metabolic activation >> Geminal Polyhaloalkane Derivatives 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 >> Haloalkenes with Electron-Withdrawing Groups OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom >> Haloalkane Derivatives with Labile Halogen OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom >> Sulfonates and Sulfates OR SN2 >> Alkylation, ring opening SN2 reaction OR SN2 >> Alkylation, ring opening SN2 reaction >> Four- and Five-Membered Lactones OR SN2 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Quinoline Derivatives OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Specific Acetate Esters OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation >> Geminal Polyhaloalkane Derivatives OR SN2 >> SN2 at an activated carbon atom OR SN2 >> SN2 at an activated carbon atom >> Quinoline Derivatives OR SN2 >> SN2 at sp3 and activated sp2 carbon atom OR SN2 >> SN2 at sp3 and activated sp2 carbon atom >> Polarized Haloalkene Derivatives OR SN2 >> SN2 at sp3-carbon atom OR SN2 >> SN2 at sp3-carbon atom >> Alpha-Haloethers by DNA binding by OASIS v.1.3

Domain logical expression index: "h"

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

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Non binder, impaired OH or NH2 group OR Non binder, MW>500 OR Non binder, non cyclic structure OR Strong binder, OH group OR Very strong binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Class 3 (unspecific reactivity) by Acute aquatic toxicity classification by Verhaar (Modified) ONLY

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Esters by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Halo Ketones (2 free H) by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Esters by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Substituted Ureas OR Surfactants-Nonionic by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as Esters by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as Pyrazoles/Pyrroles by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "q"

Referential boundary: The target chemical should be classified as Aromatic-H AND Benzene AND -C=CH  [alkenyl hydrogen] AND -CH2-  [linear] AND Ester   [-C(=O)-O-C] AND Unsubstituted phenyl group (C6H5-) by Bioaccumulation - metabolism alerts

Domain logical expression index: "r"

Referential boundary: The target chemical should be classified as Urea   [N-C(=O)-N] by Bioaccumulation - metabolism alerts

Domain logical expression index: "s"

Referential boundary: The target chemical should be classified as Aromatic-H AND Benzene AND -C=CH  [alkenyl hydrogen] AND -CH2-  [linear] AND Ester   [-C(=O)-O-C] AND Unsubstituted phenyl group (C6H5-) by Bioaccumulation - metabolism alerts

Domain logical expression index: "t"

Referential boundary: The target chemical should be classified as Triazole Ring by Bioaccumulation - metabolism alerts

Domain logical expression index: "u"

Referential boundary: The target chemical should be classified as Aromatic-H AND Benzene AND -C=CH  [alkenyl hydrogen] AND -CH2-  [linear] AND Ester   [-C(=O)-O-C] AND Unsubstituted phenyl group (C6H5-) by Bioaccumulation - metabolism alerts

Domain logical expression index: "v"

Referential boundary: The target chemical should be classified as Ketone   [-C-C(=O)-C-] by Bioaccumulation - metabolism alerts

Domain logical expression index: "w"

Referential boundary: The target chemical should be classified as Aromatic-H AND Benzene AND -C=CH  [alkenyl hydrogen] AND -CH2-  [linear] AND Ester   [-C(=O)-O-C] AND Unsubstituted phenyl group (C6H5-) by Bioaccumulation - metabolism alerts

Domain logical expression index: "x"

Referential boundary: The target chemical should be classified as Linear C4 terminal chain  [CCC-CH3] by Bioaccumulation - metabolism alerts

Domain logical expression index: "y"

Referential boundary: The target chemical should be classified as Bioavailable by Lipinski Rule Oasis ONLY

Domain logical expression index: "z"

Referential boundary: The target chemical should be classified as Group 14 - Carbon C AND Group 16 - Oxygen O by Chemical elements

Domain logical expression index: "aa"

Referential boundary: The target chemical should be classified as Group 15 - Nitrogen N by Chemical elements

Domain logical expression index: "ab"

Referential boundary: The target chemical should be classified as Not categorized by Repeated dose (HESS)

Domain logical expression index: "ac"

Referential boundary: The target chemical should be classified as Allyl esters (Hepatotoxicity) Rank A OR Chlorphentermine (Hepatotoxicity) Alert OR Phthalate esters (Testicular toxicity) Rank C by Repeated dose (HESS)

Domain logical expression index: "ad"

Referential boundary: The target chemical should be classified as (!Undefined)Group All Lipid Solubility < 0.01 g/kg AND (!Undefined)Group C Surface Tension > 62 mN/m by Skin irritation/corrosion Exclusion rules by BfR

Domain logical expression index: "ae"

Referential boundary: The target chemical should be classified as Group C Melting Point > 55 C OR Group C Vapour Pressure < 0.0001 Pa OR Group CHal Melting Point > 65 C by Skin irritation/corrosion Exclusion rules by BfR

Domain logical expression index: "af"

Referential boundary: The target chemical should be classified as Aldehyde Type Compounds by Oncologic Primary Classification

Domain logical expression index: "ag"

Referential boundary: The target chemical should be classified as Not classified by Oncologic Primary Classification

Domain logical expression index: "ah"

Referential boundary: The target chemical should be classified as Aldehyde Type Compounds by Oncologic Primary Classification

Domain logical expression index: "ai"

Referential boundary: The target chemical should be classified as Alpha, beta-Haloether Reactive Functional Groups by Oncologic Primary Classification

Domain logical expression index: "aj"

Parametric boundary:The target chemical should have a value of log Kow which is >= 0.187

Domain logical expression index: "ak"

Parametric boundary:The target chemical should have a value of log Kow which is <= 3.4

Conclusions:
Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the short term toxicity on aquatic invertebrate predicted for Cinnamyl formate (CAS: 104-65-4). Effect concentration i.e EC50 value estimated to be 148.28 mg/l for Daphnia magna for 48 hrs duration. It can be concluded that the Cinnamyl formate (CAS: 104-65-4) is likely to be not toxic to aquatic invertebrates, hence it can be considered to be “not classified” as per the CLP classification criteria for aquatic environment.
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 closest read across substances, the short term toxicity on aquatic invertebrate predicted for Cinnamyl formate (CAS: 104-65-4). Effect concentration i.e EC50 value estimated to be 148.28 mg/l for Daphnia magna for 48 hrs duration. It can be concluded that the Cinnamyl formate (CAS: 104-65-4) is likely to be not toxic to aquatic invertebrates, hence it can be considered to be “not classified” as per the CLP classification criteria for aquatic environment.

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 closest read across substances, the short term toxicity on aquatic invertebrate predicted for Cinnamyl formate (CAS: 104-65-4). Effect concentration i.e EC50 value estimated to be 148.28 mg/l for Daphnia magna for 48 hrs duration. It can be concluded that the Cinnamyl formate (CAS: 104-65-4) is likely to be not toxic to aquatic invertebrates, hence it can be considered to be “not classified” as per the CLP classification criteria for aquatic environment.

Key value for chemical safety assessment

Fresh water invertebrates

Fresh water invertebrates
Effect concentration:
148.28 mg/L

Additional information

Following studies include the predicted data and experimental study for the target chemical and structurally similar read across to conclude the toxicity extent of Cinnamyl formate (CAS: 104-65-4) towards aquatic invertebrate is summarized as follows:

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the short term toxicity on aquatic invertebrate predicted for Cinnamyl formate (CAS: 104-65-4). Effect concentration i.e EC50 value estimated to be 148.28 mg/l for Daphnia magna for 48 hrs duration. It can be concluded that the Cinnamyl formate (CAS: 104-65-4) is likely to be not toxic to aquatic invertebrates, hence it can be considered to be “not classified” as per the CLP classification criteria for aquatic environment.

The predicted results for target assisted by experimental data of read across 2-phenylethyl propanoate; Phenethyl propionate (CAS:122 -70 -3) from the publication Pakistan journal of zoologyT 2007, suggests that the naturally occurring compounds including target chemical 2-phenylethyl propanoate have been tested for molluscicidal activity against the fresh water snail, Biomphalaria alexandrina.The recommended World Health Organization bioassay procedure (WHO, 1965), was used for the evaluation of 2-phenylethyl propanoate on B. alexandrina.

For experimentBiomphalaria alexandrina species8mm ± 2mm diameter were collected from fresh water ponds at Kafr El-Dwar, Behera Governorate, Egypt and were maintained in glass aquaria oxygenated for one hour daily, one week before testing. The tests were performed in 150 ml glass beakers with ten adult healthy snails per assay. Each chemical was mixed with Tween 20, to ensure complete solubility of the chemical in water. The mixture was added to the glass beaker filled up to 100 ml of the dechlorinated water to give the desired concentration (w/v) up to 400 μg/ml for chemical.

The snails were exposed for 24 h to different concentrations of compounds or their mixture with PB and then transferred to dechlorinated water for another 48 h. Percentage kill were recorded after 72 h. Percentage mortality was corrected using Abbott's formula (Abbott, 1925). Toxicity parameters for each treatment were computed according to the probit-analysis method by Finney (1971).

According to experimental result the lethal concentration (LC50) value of phenethyl propionate in aquatic invertebrate [Biomphalaria alexandrina ] in a 72 hr study on the basis of mortality effect was found to be 296.27 mg/L. It can be concluded fom the value that the phenethyl propionate is not toxic to the aquatic invertebrate and can be considered as "not classified" as per the classifiecation criteria.

Further it is supported by the another experimental study of structurally similar read across Propyl acetate (CAS:109-60-4) from publication Zeitschrift für Wasser und Abwasserforschung 1982 also suggests that the Short-term toxicity to aquatic invertebrates test was carried out for Propyl acetate to study the effects on aquatic environment.. Behavior Equilibriumeffects was measured during the test. Effective concentration EC50 to 50% ofDaphnia magna for Propyl acetate is 318 mg/LIt can be concluded from the value that the Propyl acetate is not toxic to the aquatic invertebrate and can be considered as “not classified per the classification criteria for aquatic environment.

Thus based on the effect concentrations which is in the range 148.28 mg/l to318 mg/lgive the conclusion that test substanceCinnamyl formate (CAS: 104-65-4)is likely to be not toxic to aquatic invertebrate at environmentally relevant concentrations and applying weight of evidence approach it can be considered to be “not classified” as per the CLP classification criteria.