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Record Information
Version2.0
Creation Date2013-04-25 07:56:55 UTC
Update Date2014-12-24 20:26:34 UTC
Accession NumberT3D3941
Identification
Common NameTriflusulfuron-methyl
ClassSmall Molecule
DescriptionTriflusulfuron-methyl is a selective postemergence sulfonylurea herbicide for the control of annual and perennial broadleaf weeds and grasses in sugar beets (Beta vulgaris). Similar to other sulfonylureas, the site of action of triflusulfuron methyl is acetolactate synthase (ALS), an enzyme involved in branched-chain amino acid biosynthesis.
Compound Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Herbicide
  • Organic Compound
  • Organofluoride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H19F3N6O6S
Average Molecular Mass492.430 g/mol
Monoisotopic Mass492.104 g/mol
CAS Registry Number126535-15-7
IUPAC Namemethyl 2-[({[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoyl}amino)sulfonyl]-3-methylbenzoate
Traditional Nametriflusulfuron-methyl
SMILESCOC(=O)C1=C(C(C)=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=NC(OCC(F)(F)F)=N1)N(C)C
InChI IdentifierInChI=1S/C17H19F3N6O6S/c1-9-6-5-7-10(12(27)31-4)11(9)33(29,30)25-15(28)22-13-21-14(26(2)3)24-16(23-13)32-8-17(18,19)20/h5-7H,8H2,1-4H3,(H2,21,22,23,24,25,28)
InChI KeyInChIKey=IMEVJVISCHQJRM-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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassSulfonylureas
Direct ParentS-triazinyl-2-sulfonylureas
Alternative Parents
Substituents
  • S-triazinyl-2-sulfonylurea
  • Benzenesulfonamide
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzenesulfonyl group
  • Alkoxy-s-triazine
  • Benzoyl
  • Dialkylarylamine
  • Alkyl aryl ether
  • Aminotriazine
  • Amino-1,3,5-triazine
  • Toluene
  • N-aliphatic s-triazine
  • 1,3,5-triazine
  • Monocyclic benzene moiety
  • Benzenoid
  • Triazine
  • Heteroaromatic compound
  • Methyl ester
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Carboxylic acid ester
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic oxide
  • Carbonyl group
  • Alkyl fluoride
  • Organopnictogen compound
  • Organic oxygen compound
  • Organohalogen compound
  • Organofluoride
  • Organooxygen compound
  • Organosulfur compound
  • Alkyl halide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP2.58ALOGPS
logP3.82ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)1.28ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area152.71 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity112.62 m³·mol⁻¹ChemAxon
Polarizability44.19 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p9-3290400000-c08e4438f00882703eaaJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-000i-0190000000-88fa8ce5acf0f5607b6cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-000i-0490000000-6787ed88169b889b4c24JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-03fs-0900000000-2621452d6a9f50bdd17fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0002-0910000000-6207aa8acf303fecd873JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0090000000-9b4f94f85638316b6016JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-03di-0090000000-0fd577deb3d0d3deaafdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-03di-1090000000-6f0fcc20545568c6f124JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-01ot-9140000000-8441dc974f092c459306JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-0091800000-5086fb002e0f72402381JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0590200000-c2d4aa19224d8c6533adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fi0-5940000000-69df3e1037ac1e0f7feeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000x-0060900000-f6c80327ef12225a78b6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ai-3090000000-cbe665bffa4aee6b2b80JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g4i-7590000000-b86a77d31894a3d6d89eJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID92434
ChEMBL IDCHEMBL2143050
ChemSpider ID83452
KEGG IDC18901
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3941.pdf
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

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
TypeValueAssay TypeAssay Source
AC501.48 uMBSK_3C_uPAR_downBioSeek
AC501.48 uMBSK_BE3C_uPAR_upBioSeek
References
  1. 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 ]
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
TypeValueAssay TypeAssay Source
AC505.55 uMCLZD_CYP1A1_48CellzDirect
References
  1. 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 ]
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC506.36 uMCLZD_CYP1A2_6CellzDirect
AC509.64 uMCLZD_CYP1A2_24CellzDirect
AC508.39 uMCLZD_CYP1A2_48CellzDirect
References
  1. 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 ]
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
TypeValueAssay TypeAssay Source
AC508.74 uMCLZD_CYP2B6_6CellzDirect
AC509.32 uMCLZD_CYP2B6_24CellzDirect
AC509.75 uMCLZD_CYP2B6_48CellzDirect
References
  1. 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 ]
General Function:
Identical protein binding
Specific Function:
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name:
ADORA2A
Uniprot ID:
P29274
Molecular Weight:
44706.925 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.00 uMNVS_GPCR_hAdoRA2aNovascreen
References
  1. 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 ]