T3DB: Fluroxypyr-meptyl

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (10)XML

Targets (10)

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

T3D3849

Identification

Common Name

Fluroxypyr-meptyl

Class

Small Molecule

Description

Fluroxypyr-meptyl is an esterified form of the herbicide fluroxypyr (it is a pro-herbicide, similar to a pro-drug). After predominantly foliar uptake, the ester is hydrolyzed to the parent acid, which is the herbicidally active form. Fluroxypyr is a pyridine-based herbicide used to control established broadleaf weeds and woody brush. It is registered for use on corn, wheat, barley, oats, sorghum, forage, hay, onions, fallow cropland, industrial sites, and rights-of-way, as well as home lawns and recreational sites such as golf courses, parks, and sports fields

Compound Type

Amine
Ester
Ether
Herbicide
Industrial/Workplace Toxin
Organic Compound
Organochloride
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
1-Methylheptyl ((4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxy)acetate
1-Methylheptyl (4-amino-3,5-dichloro-6-fluoro-2-pyridyloxy)acetate
1-Methylheptyl [(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxy]acetate
2-Octanyl [(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]acetate
Fluroxypyr 1-methylheptyl ester
Fluroxypyr methyl heptyl
methylheptyl 2-(4-amino-3,5-dichloro-6-fluoro-2-pyridyloxy)acetate
octan-2-yl 2-[(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxy]acetate
Spotlight
Starane
[(4-amino-3,5-dichloro-6fluoro-2-pyridinyl)oxy]acetic acid

Chemical Formula

C₁₅H₂₁Cl₂FN₂O₃

Average Molecular Mass

367.243 g/mol

Monoisotopic Mass

366.091 g/mol

CAS Registry Number

81406-37-3

IUPAC Name

octan-2-yl 2-[(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxy]acetate

Traditional Name

fluroxypyr-meptyl

SMILES

CCCCCCC(C)OC(=O)COC1=NC(F)=C(Cl)C(N)=C1Cl

InChI Identifier

InChI=1S/C15H21Cl2FN2O3/c1-3-4-5-6-7-9(2)23-10(21)8-22-15-12(17)13(19)11(16)14(18)20-15/h9H,3-8H2,1-2H3,(H2,19,20)

InChI Key

InChIKey=OLZQTUCTGLHFTQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as polyhalopyridines. These are organic compounds containing a pyridine ring substituted at two or more positions by a halogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Halopyridines

Direct Parent

Polyhalopyridines

Alternative Parents

Substituents

Polyhalopyridine
Alkyl aryl ether
Aminopyridine
2-halopyridine
Aryl chloride
Aryl fluoride
Aryl halide
Heteroaromatic compound
Amino acid or derivatives
Carboxylic acid ester
Azacycle
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organohalogen compound
Organochloride
Organofluoride
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Amine
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

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	0.012 g/L	ALOGPS
logP	5.32	ALOGPS
logP	4.81	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.44 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	89.17 m³·mol⁻¹	ChemAxon
Polarizability	36.52 Å³	ChemAxon
Number of Rings	1	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	splash10-030r-0914000000-ac0a6a543e7b122ffd9a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3921000000-a0b1b7760cccfbc107cc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0229-4900000000-cc89c1dbe7b794a924b0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-02vi-0956000000-f0d25977e2782835897c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0943000000-6ba181cef5432c0c5759	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03na-3920000000-9579283e036c28e699ca	2016-08-03	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

Not Available

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

54745

ChEMBL ID

CHEMBL1882270

ChemSpider ID

49451

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

T3D3849.pdf

General References

Not Available

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. 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_KF3CT_MCP1_up	BioSeek

References

Target Details

2. 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	1.48 uM	BSK_KF3CT_IP10_up	BioSeek

References

Target Details

3. C-X-C motif chemokine 9

General Function:: Cytokine activity
Specific Function:: Cytokine that affects the growth, movement, or activation state of cells that participate in immune and inflammatory response. Chemotactic for activated T-cells. Binds to CXCR3.
Gene Name:: CXCL9
Uniprot ID:: Q07325
Molecular Weight:: 14018.72 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.48 uM	BSK_hDFCGF_MIG_up	BioSeek

References

Target Details

4. Macrophage colony-stimulating factor 1

General Function:: Protein homodimerization activity
Specific Function:: Cytokine that plays an essential role in the regulation of survival, proliferation and differentiation of hematopoietic precursor cells, especially mononuclear phagocytes, such as macrophages and monocytes. Promotes the release of proinflammatory chemokines, and thereby plays an important role in innate immunity and in inflammatory processes. Plays an important role in the regulation of osteoclast proliferation and differentiation, the regulation of bone resorption, and is required for normal bone development. Required for normal male and female fertility. Promotes reorganization of the actin cytoskeleton, regulates formation of membrane ruffles, cell adhesion and cell migration. Plays a role in lipoprotein clearance.
Gene Name:: CSF1
Uniprot ID:: P09603
Molecular Weight:: 60178.885 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.48 uM	BSK_hDFCGF_MCSF_up	BioSeek

References

Target Details

5. Matrix metalloproteinase-9

General Function:: Zinc ion binding
Specific Function:: May play an essential role in local proteolysis of the extracellular matrix and in leukocyte migration. Could play a role in bone osteoclastic resorption. Cleaves KiSS1 at a Gly-|-Leu bond. Cleaves type IV and type V collagen into large C-terminal three quarter fragments and shorter N-terminal one quarter fragments. Degrades fibronectin but not laminin or Pz-peptide.
Gene Name:: MMP9
Uniprot ID:: P14780
Molecular Weight:: 78457.51 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.48 uM	BSK_KF3CT_MMP9_up	BioSeek

References

Target Details

6. Beta-secretase 1

General Function:: Peptidase activity
Specific Function:: Responsible for the proteolytic processing of the amyloid precursor protein (APP). Cleaves at the N-terminus of the A-beta peptide sequence, between residues 671 and 672 of APP, leads to the generation and extracellular release of beta-cleaved soluble APP, and a corresponding cell-associated C-terminal fragment which is later released by gamma-secretase.
Gene Name:: BACE1
Uniprot ID:: P56817
Molecular Weight:: 55710.28 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	3.70 uM	NVS_ENZ_hBACE	Novascreen
AC50	3.18 uM	NVS_ENZ_hBACE	Novascreen

References

Target Details

7. Interleukin-1 alpha

General Function:: Cytokine activity
Specific Function:: Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells.
Gene Name:: IL1A
Uniprot ID:: P01583
Molecular Weight:: 30606.29 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.44 uM	BSK_BE3C_IL1a_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_hDFCGF_IL8_down	BioSeek

References

Target Details

9. 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	4.65 uM	CLZD_CYP2B6_6	CellzDirect

References

Target Details

10. Cytochrome P450 2C19

General Function:: Steroid hydroxylase activity
Specific Function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular Weight:: 55930.545 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	5.80 uM	NVS_ADME_hCYP2C19	Novascreen
AC50	4.74 uM	NVS_ADME_hCYP2C19	Novascreen

References

Fluroxypyr-meptyl (T3D3849)

Structure for T3D3849: Fluroxypyr-meptyl

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