6-Deisopropylatrazine
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Basic Info
| Common Name | 6-Deisopropylatrazine(F05022) |
| 2D Structure | |
| Description | 6-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. |
| FRCD ID | F05022 |
| CAS Number | 1007-28-9 |
| PubChem CID | 13878 |
| Formula | C5H8ClN5 |
| IUPAC Name | 6-chloro-2-N-ethyl-1,3,5-triazine-2,4-diamine |
| InChI Key | IVENSCMCQBJAKW-UHFFFAOYSA-N |
| InChI | InChI=1S/C5H8ClN5/c1-2-8-5-10-3(6)9-4(7)11-5/h2H2,1H3,(H3,7,8,9,10,11) |
| Canonical SMILES | CCNC1=NC(=NC(=N1)N)Cl |
| Isomeric SMILES | CCNC1=NC(=NC(=N1)N)Cl |
| Synonyms |
Deisopropylatrazine
6-Deisopropylatrazine
1007-28-9
Atrazine-desisopropyl
deethylsimazine
Desethylsimazine
desisopropylatrazine
Desisopropyl Atrazine
Caswell No. 033F
G 28279
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Triazines |
| Subclass | Aminotriazines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 1,3,5-triazine-2,4-diamines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| 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 |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 173.604 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Complexity | 121 |
| Monoisotopic Mass | 173.047 |
| Exact Mass | 173.047 |
| XLogP | 1.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8840 |
| Human Intestinal Absorption | HIA+ | 0.9932 |
| Caco-2 Permeability | Caco2+ | 0.5460 |
| P-glycoprotein Substrate | Non-substrate | 0.6572 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9572 |
| Non-inhibitor | 0.9089 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7564 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6917 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8879 |
| CYP450 2D6 Substrate | Non-substrate | 0.8431 |
| CYP450 3A4 Substrate | Non-substrate | 0.7406 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7568 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9532 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8438 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7316 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9541 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8776 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8587 |
| Non-inhibitor | 0.8874 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.8230 |
| Fish Toxicity | Low FHMT | 0.9144 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9712 |
| Honey Bee Toxicity | Low HBT | 0.8525 |
| Biodegradation | Not ready biodegradable | 0.9926 |
| Acute Oral Toxicity | III | 0.5731 |
| Carcinogenicity (Three-class) | Warning | 0.4510 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1554 | LogS |
| Caco-2 Permeability | 1.1441 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6453 | LD50, mol/kg |
| Fish Toxicity | 2.5008 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.0413 | pIGC50, ug/L |
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
- 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 ]