T3DB: Flufenpyr-ethyl

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (9)XML

Targets (9)

Record Information

Version

2.0

Creation Date

2013-04-25 07:56:51 UTC

Update Date

2014-12-24 20:26:33 UTC

Accession Number

T3D3844

Identification

Common Name

Flufenpyr-ethyl

Class

Small Molecule

Description

Flufenpyr-ethyl is a contact herbicide for use on potatoes, maize, soya and wheat to control broad-leaved weeds.

Compound Type

Ester
Ether
Herbicide
Organic Compound
Organochloride
Organofluoride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
Ethyl 2-chloro-5-[1,6-dihydro-5-methyl-6-oxo-4-(trifluoromethyl)pyridazin-1-yl]-4-fluorophenoxyacetate
Ethyl {2-chloro-4-fluoro-5-[5-methyl-6-oxo-4-(trifluoromethyl)-1(6H)-pyridazinyl]phenoxy}acetate
Ethyl {2-chloro-4-fluoro-5-[5-methyl-6-oxo-4-(trifluoromethyl)pyridazin-1(6H)-yl]phenoxy}acetate

Chemical Formula

C₁₆H₁₃ClF₄N₂O₄

Average Molecular Mass

408.732 g/mol

Monoisotopic Mass

408.050 g/mol

CAS Registry Number

188489-07-8

IUPAC Name

ethyl 2-{2-chloro-4-fluoro-5-[5-methyl-6-oxo-4-(trifluoromethyl)-1,6-dihydropyridazin-1-yl]phenoxy}acetate

Traditional Name

ethyl 2-{2-chloro-4-fluoro-5-[5-methyl-6-oxo-4-(trifluoromethyl)pyridazin-1-yl]phenoxy}acetate

SMILES

CCOC(=O)COC1=CC(N2N=CC(=C(C)C2=O)C(F)(F)F)=C(F)C=C1Cl

InChI Identifier

InChI=1S/C16H13ClF4N2O4/c1-3-26-14(24)7-27-13-5-12(11(18)4-10(13)17)23-15(25)8(2)9(6-22-23)16(19,20)21/h4-6H,3,7H2,1-2H3

InChI Key

InChIKey=DNUAYCRATWAJQE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Phenoxyacetic acid derivatives

Alternative Parents

Substituents

Phenoxyacetate
Phenoxy compound
Phenol ether
Alkyl aryl ether
Chlorobenzene
Fluorobenzene
Pyridazinone
Halobenzene
Aryl chloride
Aryl fluoride
Aryl halide
Pyridazine
Heteroaromatic compound
Carboxylic acid ester
Lactam
Carboxylic acid derivative
Azacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organooxygen compound
Alkyl halide
Alkyl fluoride
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organic oxygen compound
Organohalogen compound
Organochloride
Organofluoride
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Off-white coloured powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0012 g/L	ALOGPS
logP	3.97	ALOGPS
logP	3.05	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	68.2 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.37 m³·mol⁻¹	ChemAxon
Polarizability	34.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-2009600000-2ae9a0cbefdfb5a01529	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-074j-3109200000-8e77d247d9b743c46e9a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fer-3906000000-7dd204b404cefd7eb407	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-3009500000-eab80700da8371342fc7	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1219000000-0cd45e7c6ddb6771bb91	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00bd-4954000000-e746116dd4bbbe6e353c	2016-08-04	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

'EP A does not have, at this time, available data to determine whether flufenpyr-ethyl has a common mechanism of toxicity with other substances.' (2)

Metabolism

Flufenpyr-ethyl's known metabolites in animals include S-3135-acid ([2-chloro-4-fluoro-5-(5-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyridazin-1-yl)phenoxy]-acetic acid) and S-3153-acid-5-CH2OH ([2-chloro-4-fluoro-5-(5-hydroxymethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyridazin-1-yl)phenoxy]-acetic acid) (1).

Toxicity Values

LD50: > 5,000 mg/kg (acute oral, rat) (2); LD50: > 5,000 mg/kg (acute dermal, rat) (2); > 5.0 mg/L (acute inhalation, rat) (2)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

3083546

ChEMBL ID

Not Available

ChemSpider ID

2340733

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

PPDB: Pesticide Properties DataBase - flufenpyr-ethyl (Ref: S 3153) [Link]
US EPA. Memorandum: Flufenpyr-Ethyl in/on Field Corn, Soybeans and Sugarcane. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Cytochrome P450 4F12

General Function:: Leukotriene-b4 20-monooxygenase activity
Specific Function:: Catalyzes leukotriene B4 omega-hydroxylation and arachidonic acid omega-hydroxylation but with an activity much lower than that of CYP4F2. Catalyzes the hydroxylation of the antihistamine ebastine.
Gene Name:: CYP4F12
Uniprot ID:: Q9HCS2
Molecular Weight:: 60269.165 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	0.06 uM	NVS_ADME_hCYP4F12_Activator	Novascreen
AC50	0.07 uM	NVS_ADME_hCYP4F12_Activator	Novascreen
AC50	0.07 uM	NVS_ADME_hCYP4F12_Activator	Novascreen

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

2. C-C motif chemokine 2

General Function:: Not Available
Specific Function:: Not Available
Gene Name:: CCL2
Uniprot ID:: P13500
Molecular Weight:: 11024.87 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.48 uM	BSK_LPS_MCP1_up	BioSeek

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

3. Urokinase plasminogen activator surface receptor

General Function:: Urokinase plasminogen activator receptor activity
Specific Function:: Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
Gene Name:: PLAUR
Uniprot ID:: Q03405
Molecular Weight:: 36977.62 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.48 uM	BSK_BE3C_uPAR_up	BioSeek

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

4. Cytochrome P450 2B6

General Function:: Steroid hydroxylase activity
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular Weight:: 56277.81 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	3.15 uM	CLZD_CYP2B6_6	CellzDirect
AC50	7.43 uM	CLZD_CYP2B6_24	CellzDirect

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

5. C-X-C motif chemokine 10

General Function:: Receptor binding
Specific Function:: Chemotactic for monocytes and T-lymphocytes. Binds to CXCR3.
Gene Name:: CXCL10
Uniprot ID:: P02778
Molecular Weight:: 10880.915 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.44 uM	BSK_BE3C_IP10_up	BioSeek

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

6. Interleukin-8

General Function:: Interleukin-8 receptor binding
Specific Function:: IL-8 is a chemotactic factor that attracts neutrophils, basophils, and T-cells, but not monocytes. It is also involved in neutrophil activation. It is released from several cell types in response to an inflammatory stimulus. IL-8(6-77) has a 5-10-fold higher activity on neutrophil activation, IL-8(5-77) has increased activity on neutrophil activation and IL-8(7-77) has a higher affinity to receptors CXCR1 and CXCR2 as compared to IL-8(1-77), respectively.
Gene Name:: CXCL8
Uniprot ID:: P10145
Molecular Weight:: 11097.98 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.44 uM	BSK_SAg_IL8_up	BioSeek

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

7. Interstitial collagenase

General Function:: Zinc ion binding
Specific Function:: Cleaves collagens of types I, II, and III at one site in the helical domain. Also cleaves collagens of types VII and X. In case of HIV infection, interacts and cleaves the secreted viral Tat protein, leading to a decrease in neuronal Tat's mediated neurotoxicity.
Gene Name:: MMP1
Uniprot ID:: P03956
Molecular Weight:: 54006.61 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.44 uM	BSK_hDFCGF_MMP1_up	BioSeek

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

8. Plasminogen activator inhibitor 1

General Function:: Serine-type endopeptidase inhibitor activity
Specific Function:: Serine protease inhibitor. This inhibitor acts as 'bait' for tissue plasminogen activator, urokinase, protein C and matriptase-3/TMPRSS7. Its rapid interaction with PLAT may function as a major control point in the regulation of fibrinolysis.
Gene Name:: SERPINE1
Uniprot ID:: P05121
Molecular Weight:: 45059.695 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.44 uM	BSK_hDFCGF_PAI1_up	BioSeek

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

9. Cytochrome P450 3A4

General Function:: Vitamin d3 25-hydroxylase activity
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular Weight:: 57342.67 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	7.86 uM	CLZD_CYP3A4_6	CellzDirect
AC50	6.69 uM	CLZD_CYP3A4_24	CellzDirect
AC50	9.98 uM	CLZD_CYP3A4_48	CellzDirect

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Flufenpyr-ethyl (T3D3844)

Structure for T3D3844: Flufenpyr-ethyl

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References