T3DB: Pyraflufen-ethyl

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (14)XML

Targets (14)

Record Information

Version

2.0

Creation Date

2014-08-29 06:51:45 UTC

Update Date

2014-12-24 20:26:52 UTC

Accession Number

T3D4531

Identification

Common Name

Pyraflufen-ethyl

Class

Small Molecule

Description

Pyraflufen-ethyl is a herbicide used to control broad-leaved weeds and grasses in crops being selective with contact action.

Compound Type

Ester
Ether
Herbicide
Organic Compound
Organochloride
Organofluoride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym
ethyl 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)-4-fluorophenoxyacetate, ethyl [2-chloro-5-[4-chloro-5-(difluoromethoxy)-1-methyl-1H-pyrazol-3-yl]-4-fluorophenoxy]acetate

Chemical Formula

C₁₅H₁₃Cl₂F₃N₂O₄

Average Molecular Mass

413.176 g/mol

Monoisotopic Mass

412.020 g/mol

CAS Registry Number

129630-19-9

IUPAC Name

ethyl 2-{2-chloro-5-[4-chloro-5-(difluoromethoxy)-1-methyl-1H-pyrazol-3-yl]-4-fluorophenoxy}acetate

Traditional Name

pyraflufen-ethyl

SMILES

CCOC(=O)COC1=C(Cl)C=C(F)C(=C1)C1=NN(C)C(OC(F)F)=C1Cl

InChI Identifier

InChI=1S/C15H13Cl2F3N2O4/c1-3-24-11(23)6-25-10-4-7(9(18)5-8(10)16)13-12(17)14(22(2)21-13)26-15(19)20/h4-5,15H,3,6H2,1-2H3

InChI Key

InChIKey=APTZNLHMIGJTEW-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Pyrazoles

Direct Parent

Phenylpyrazoles

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazoles (CHEBI:81828 )
ring assembly (CHEBI:81828 )
Pyrazole herbicides (C18554 )

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

White 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	0.0064 g/L	ALOGPS
logP	4.69	ALOGPS
logP	4.47	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	0.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	62.58 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	97.34 m³·mol⁻¹	ChemAxon
Polarizability	35.7 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	splash10-03fr-1009500000-35e44b23cc255e4f7a3e	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02dj-4009200000-4e0e23b65504b62f8b59	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-3169000000-9013179d972a4d304e03	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3109500000-ba328bd7461877b3e6a8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-1039000000-040f3214324709306742	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kb-2964000000-10365530a8547e9351c6	2016-08-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.40 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

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

ChEMBL ID

ChemSpider ID

KEGG ID

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

T3D4531.pdf

General References

Not Available

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Nuclear receptor subfamily 1 group I member 2

General Function:: Zinc ion binding
Specific Function:: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:: NR1I2
Uniprot ID:: O75469
Molecular Weight:: 49761.245 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	0.02 uM	NVS_NR_hPXR	Novascreen

References

Target Details

2. Early activation antigen CD69

General Function:: Transmembrane signaling receptor activity
Specific Function:: Involved in lymphocyte proliferation and functions as a signal transmitting receptor in lymphocytes, natural killer (NK) cells, and platelets.
Gene Name:: CD69
Uniprot ID:: Q07108
Molecular Weight:: 22559.25 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.48 uM	BSK_SAg_CD69_up	BioSeek

References

Target Details

3. 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	1.48 uM	BSK_hDFCGF_MMP1_up	BioSeek

References

Target Details

4. 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

Target Details

5. 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	4.09 uM	CLZD_CYP2B6_6	CellzDirect

References

Target Details

6. ADP-ribosyl cyclase/cyclic ADP-ribose hydrolase 1

General Function:: Transferase activity
Specific Function:: Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
Gene Name:: CD38
Uniprot ID:: P28907
Molecular Weight:: 34328.145 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.44 uM	BSK_SAg_CD38_up	BioSeek

References

Target Details

7. 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	4.44 uM	BSK_SAg_MCP1_up	BioSeek

References

Target Details

8. 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_LPS_IL8_down	BioSeek

References

Target Details

9. Tissue factor

General Function:: Protease binding
Specific Function:: Initiates blood coagulation by forming a complex with circulating factor VII or VIIa. The [TF:VIIa] complex activates factors IX or X by specific limited protolysis. TF plays a role in normal hemostasis by initiating the cell-surface assembly and propagation of the coagulation protease cascade.
Gene Name:: F3
Uniprot ID:: P13726
Molecular Weight:: 33067.3 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.44 uM	BSK_3C_TissueFactor_down	BioSeek

References

Target Details

10. Bile salt sulfotransferase

General Function:: Sulfotransferase activity
Specific Function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name:: SULT2A1
Uniprot ID:: Q06520
Molecular Weight:: 33779.57 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.54 uM	CLZD_SULT2A1_24	CellzDirect

References

Target Details

11. UDP-glucuronosyltransferase 1-1

General Function:: Steroid binding
Specific Function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular Weight:: 59590.91 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.80 uM	CLZD_UGT1A1_24	CellzDirect
AC50	4.77 uM	CLZD_UGT1A1_48	CellzDirect

References

Target Details

12. 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	5.03 uM	CLZD_CYP3A4_6	CellzDirect
AC50	7.28 uM	CLZD_CYP3A4_24	CellzDirect

References

Target Details

13. Aryl hydrocarbon receptor

General Function:: Transcription regulatory region dna binding
Specific Function:: Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
Gene Name:: AHR
Uniprot ID:: P35869
Molecular Weight:: 96146.705 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	6.35 uM	Tox21_AhR	Tox21/NCGC

References

Target Details

14. Cytochrome P450 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular Weight:: 55627.365 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	7.41 uM	CLZD_CYP2C9_48	CellzDirect

References

Pyraflufen-ethyl (T3D4531)

Structure for T3D4531: Pyraflufen-ethyl

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