T3DB: Ethametsulfuron methyl

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (5)XML

Targets (5)

Record Information

Version

2.0

Creation Date

2014-08-29 06:51:42 UTC

Update Date

2014-12-24 20:26:51 UTC

Accession Number

T3D4501

Identification

Common Name

Ethametsulfuron methyl

Class

Small Molecule

Description

Ethametsulfuron-methyl is a selective herbicide for the control of wild mustard, stinkweed and other broad-leaved weeds especially in canola. It is moderately soluble in water, non-volatile and, based on its chemical properties, presents a high risk of leaching to groundwater. It is relatively persistent in both soil and aqueous systems. It has a low mammalian toxicity but may bio-accumulate. It has a low toxicity to birds and most aquatic species, the exception being aquatic plants including algae. It is moderately toxic to honeybees

Compound Type

Amide
Ester
Ether
Herbicide
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
Benzoic acid, 2-[[[[[4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-, methyl ester
ETHAMETSULFURON METHYL ESTER
Ethametsulfuron methyl, Methyl 2-((4-ethoxy-6-methylamino-1,3,5-triazin-2-yl)carbamoylsulfamoyl)benzoate

Chemical Formula

C₁₅H₁₈N₆O₆S

Average Molecular Mass

410.405 g/mol

Monoisotopic Mass

410.101 g/mol

CAS Registry Number

97780-06-8

IUPAC Name

methyl 2-[({[6-ethoxy-4-(methylimino)-1,4-dihydro-1,3,5-triazin-2-yl]-C-hydroxycarbonimidoyl}amino)sulfonyl]benzoate

Traditional Name

methyl 2-({[4-ethoxy-6-(methylimino)-3H-1,3,5-triazin-2-yl]-C-hydroxycarbonimidoyl}aminosulfonyl)benzoate

SMILES

CCOC1=NC(=NC)N=C(N1)N=C(O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC

InChI Identifier

InChI=1S/C15H18N6O6S/c1-4-27-15-19-12(16-2)17-13(20-15)18-14(23)21-28(24,25)10-8-6-5-7-9(10)11(22)26-3/h5-8H,4H2,1-3H3,(H3,16,17,18,19,20,21,23)

InChI Key

InChIKey=ZINJLDJMHCUBIP-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as s-triazinyl-2-sulfonylureas. These are aromatic heterocyclic compounds containing a s-triazine ring which is substituted with a urea at the ring 2-position.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Sulfonylureas

Direct Parent

S-triazinyl-2-sulfonylureas

Alternative Parents

Substituents

S-triazinyl-2-sulfonylurea
Benzenesulfonamide
Benzoate ester
Benzenesulfonyl group
Benzoic acid or derivatives
Alkoxy-s-triazine
Benzoyl
Alkyl aryl ether
Amino-1,3,5-triazine
Aminotriazine
Secondary aliphatic/aromatic amine
N-aliphatic s-triazine
Monocyclic benzene moiety
1,3,5-triazine
Triazine
Benzenoid
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Methyl ester
Aminosulfonyl compound
Heteroaromatic compound
Carbonic acid derivative
Carboxylic acid ester
Amino acid or derivatives
Secondary amine
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Azacycle
Organosulfur compound
Amine
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

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	0.068 g/L	ALOGPS
logP	1.06	ALOGPS
logP	1.41	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	1.71	ChemAxon
pKa (Strongest Basic)	0.026	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	163.4 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	97.87 m³·mol⁻¹	ChemAxon
Polarizability	38.74 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v0r-1509000000-6315f5362281fa004cbe	2021-09-24	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0932300000-3ba92e923df744559c2a	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2920000000-91a68732d056e77e7c21	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014r-3900000000-8e72fc8a3b78251b538b	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-07vu-2669400000-94918620552c8e5123f5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-2390000000-6d84098b5c046f0a6031	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03ka-9520000000-65f77d6cc1a667cf29fa	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01r2-0904300000-cdec82b37f2c12e022b4	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gba-0914000000-8e3700fb4459eec6ec79	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-2912000000-2bf3d0e899849757b543	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-0960800000-5037e06dabba736c2a94	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-2a8c65d4a11adc6f27be	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9634000000-97258290d694ced48927	2021-10-12	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

91756

ChEMBL ID

CHEMBL1885280

ChemSpider ID

82854

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

T3D4501.pdf

General References

Not Available

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. 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	0.46 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 ]

Target Details

2. Epidermal growth factor receptor

General Function:: Ubiquitin protein ligase binding
Specific Function:: Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TGFA/TGF-alpha, amphiregulin, epigen/EPGN, BTC/betacellulin, epiregulin/EREG and HBEGF/heparin-binding EGF. Ligand binding triggers receptor homo- and/or heterodimerization and autophosphorylation on key cytoplasmic residues. The phosphorylated receptor recruits adapter proteins like GRB2 which in turn activates complex downstream signaling cascades. Activates at least 4 major downstream signaling cascades including the RAS-RAF-MEK-ERK, PI3 kinase-AKT, PLCgamma-PKC and STATs modules. May also activate the NF-kappa-B signaling cascade. Also directly phosphorylates other proteins like RGS16, activating its GTPase activity and probably coupling the EGF receptor signaling to the G protein-coupled receptor signaling. Also phosphorylates MUC1 and increases its interaction with SRC and CTNNB1/beta-catenin.Isoform 2 may act as an antagonist of EGF action.
Gene Name:: EGFR
Uniprot ID:: P00533
Molecular Weight:: 134276.185 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.48 uM	BSK_hDFCGF_EGFR_down	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. 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_down	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	9.15 uM	CLZD_CYP2B6_24	CellzDirect
AC50	6.89 uM	CLZD_CYP2B6_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 ]

Target Details

5. Cytochrome P450 1A1

General Function:: Vitamin d 24-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.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular Weight:: 58164.815 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	10.00 uM	CLZD_CYP1A1_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 ]

Ethametsulfuron methyl (T3D4501)

Structure for T3D4501: Ethametsulfuron methyl

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

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Binding/Activity Constants

References