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Record Information
Version2.0
Creation Date2013-04-25 07:56:49 UTC
Update Date2014-12-24 20:26:32 UTC
Accession NumberT3D3787
Identification
Common Name6-Deisopropylatrazine
ClassSmall Molecule
Description6-Deisopropylatrazine is a chlorinated degradation product of the herbicide atrazine (6-chloro-N2-ethyl-N4-isopropyl-1, 3,5-triazine-2,4-diamine). Atrazine is a herbicide of the triazine class. Atrazine is used to prevent pre and post-emergence broadleaf weeds in crops such as maize (corn) and sugarcane and on turf, such as golf courses and residential lawns. It is one of the most widely used herbicides in the US and in Australian agriculture.] It was banned in the European Union in 2004 because of persistent groundwater contamination. As of 2001, Atrazine was the most commonly detected pesticide contaminating drinking water in the United States. Studies suggest atrazine is an endocrine disruptor and it is thought that 6-Deisopropylatrazine may also have some endocrine disruptor capacity. Pesticide degradates account for a significant portion of the pesticide/herbicide load in surface water. t is a registered US EPA substance.
Compound Type
  • Amine
  • Herbicide
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
2-amino-4-chloro-6-(Ethylamino)-S-triazine
2-amino-4-chloro-6-Ethylamino-S-triazine
2-chloro-4-amino-6-Ethylamino-S-triazine
amino-2-chloro-6-Ethylamino-S-triazine
Deisopropylatrazine
Chemical FormulaC5H8ClN5
Average Molecular Mass173.604 g/mol
Monoisotopic Mass173.047 g/mol
CAS Registry Number1007-28-9
IUPAC Name6-chloro-N2-ethyl-1,3,5-triazine-2,4-diamine
Traditional Namedeisopropylatrazine
SMILESCCNC1=NC(N)=NC(Cl)=N1
InChI IdentifierInChI=1S/C5H8ClN5/c1-2-8-5-10-3(6)9-4(7)11-5/h2H2,1H3,(H3,7,8,9,10,11)
InChI KeyInChIKey=IVENSCMCQBJAKW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,3,5-triazine-2,4-diamines. These are aromatic compounds containing a 1,3,5-triazine ring which is 2,4-disusbtituted wit amine groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTriazines
Sub ClassAminotriazines
Direct Parent1,3,5-triazine-2,4-diamines
Alternative Parents
Substituents
  • 2,4-diamine-s-triazine
  • Chloro-s-triazine
  • Halo-s-triazine
  • Secondary aliphatic/aromatic amine
  • N-aliphatic s-triazine
  • Aryl chloride
  • Aryl halide
  • 1,3,5-triazine
  • Heteroaromatic compound
  • Azacycle
  • Secondary amine
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
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 Solubility0.79 g/LALOGPS
logP1.18ALOGPS
logP1.12ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)14.94ChemAxon
pKa (Strongest Basic)3.41ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area76.72 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.56 m³·mol⁻¹ChemAxon
Polarizability16.45 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-03aaf742b698b7b15cd2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-2900000000-467e1c27971898480793JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9100000000-4f39f231d149b1619207JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-e0a3cbcd00c05fc34895JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-7900000000-50fedb4cd541572233a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9600000000-cf7a8183fdf887cdcaf4JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-9500000000-c58ade4d8021461f2763JSpectraViewer | MoNA
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 ID13878
ChEMBL IDCHEMBL1895845
ChemSpider ID13278
KEGG IDC06556
UniProt IDNot Available
OMIM ID
ChEBI ID27399
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Tran DQ, Kow KY, McLachlan JA, Arnold SF: The inhibition of estrogen receptor-mediated responses by chloro-S-triazine-derived compounds is dependent on estradiol concentration in yeast. Biochem Biophys Res Commun. 1996 Oct 3;227(1):140-6. [8858116 ]