Propazine
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Basic Info
| Common Name | Propazine(F05126) |
| 2D Structure | |
| Description | Propazine is an herbicide used for control of broadleaf weeds and annual grasses in sweet sorghum. It is applied as a spray at the time of planting or immediately following planting, but prior to weed or sorghum emergence. It is also used as a postemergence selective herbicide on carrots, celery and fennel. Propazine is classified as a slightly toxic compound in EPA toxicity class III and as a General Use Pesticide. |
| FRCD ID | F05126 |
| CAS Number | 139-40-2 |
| PubChem CID | 4937 |
| Formula | C9H16ClN5 |
| IUPAC Name | 6-chloro-2-N,4-N-di(propan-2-yl)-1,3,5-triazine-2,4-diamine |
| InChI Key | WJNRPILHGGKWCK-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H16ClN5/c1-5(2)11-8-13-7(10)14-9(15-8)12-6(3)4/h5-6H,1-4H3,(H2,11,12,13,14,15) |
| Canonical SMILES | CC(C)NC1=NC(=NC(=N1)Cl)NC(C)C |
| Isomeric SMILES | CC(C)NC1=NC(=NC(=N1)Cl)NC(C)C |
| Synonyms |
propazine
139-40-2
Prozinex
Gesamil
Milogard
Plantulin
Propazin
Primatol P
Propasin
Milo-pro
|
| Classifies |
Pollutant
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 - 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 | 229.712 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Complexity | 169 |
| Monoisotopic Mass | 229.109 |
| Exact Mass | 229.109 |
| XLogP | 2.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| 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+ | 0.8621 |
| Human Intestinal Absorption | HIA+ | 0.9739 |
| Caco-2 Permeability | Caco2+ | 0.6235 |
| P-glycoprotein Substrate | Non-substrate | 0.7295 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9290 |
| Non-inhibitor | 0.9346 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8582 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4810 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8449 |
| CYP450 2D6 Substrate | Non-substrate | 0.8127 |
| CYP450 3A4 Substrate | Non-substrate | 0.5826 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8820 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9518 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8307 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7040 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8891 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7517 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9162 |
| Non-inhibitor | 0.8736 | |
| AMES Toxicity | Non AMES toxic | 0.9556 |
| Carcinogens | Non-carcinogens | 0.8754 |
| Fish Toxicity | Low FHMT | 0.6056 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9384 |
| Honey Bee Toxicity | Low HBT | 0.7879 |
| Biodegradation | Not ready biodegradable | 0.9972 |
| Acute Oral Toxicity | III | 0.8118 |
| Carcinogenicity (Three-class) | Warning | 0.4371 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.3673 | LogS |
| Caco-2 Permeability | 1.5624 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9999 | LD50, mol/kg |
| Fish Toxicity | 1.8014 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3780 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Enhanced degradation of prometryn and other s-triazine herbicides in purecultures and wastewater by polyvinyl alcohol-sodium alginate immobilizedLeucobacter sp. JW-1. | Sci Total Environ | 2018 Feb 15 | 28963898 |
| Activity, biomass and composition of microbial communities and their degradation pathways in exposed propazine soil. | Ecotoxicol Environ Saf | 2017 Nov | 28763756 |
| Novel hydrolytic de-methylthiolation of the s-triazine herbicide prometryn byLeucobacter sp. JW-1. | Sci Total Environ | 2017 Feb 1 | 27866738 |
| Determination of triazine herbicides in fresh vegetables by dynamicmicrowave-assisted extraction coupled with homogeneous ionic liquidmicroextraction high performance liquid chromatography. | Anal Bioanal Chem | 2015 Feb | 25542578 |
| Simultaneous voltammetric determination of four triazine herbicides in watersamples with the aid of chemometrics. | J Environ Sci Health B | 2014 | 25065823 |
| A modified QuEChERS method for the determination of some herbicides in yogurt andmilk by high performance liquid chromatography. | Talanta | 2013 Feb 15 | 23598011 |
| A chemometrics approach for simultaneous determination of cyanazine and propazinebased on a carbon paste electrode modified by a molecularly imprinted polymer. | Analyst | 2012 Mar 7 | 22240717 |
| Computational design and synthesis of a high selective molecularly imprintedpolymer for voltammetric sensing of propazine in food samples. | Talanta | 2012 Jan 30 | 22284525 |
| Extraction of eight triazine and phenylurea herbicides in yogurt by ionic liquid foaming-based solvent floatation. | J Chromatogr A | 2012 Jan 27 | 22218326 |
| Determination of phenylurea and triazine herbicides in milk by microwave assistedionic liquid microextraction high-performance liquid chromatography. | Talanta | 2010 Sep 15 | 20801343 |
| Selective extraction of triazine herbicides from food samples based on acombination of a liquid membrane and molecularly imprinted polymers. | J Chromatogr A | 2009 Oct 2 | 19720380 |
| Determination of triazine herbicides in fruits and vegetables using dispersivesolid-phase extraction coupled with LC-MS. | J Sep Sci | 2008 Apr | 18338404 |
| Clean-up of triazines in vegetable extracts by molecularly-imprinted solid-phase extraction using a propazine-imprinted polymer. | Anal Bioanal Chem | 2003 Jun | 12739096 |
| Determination of atrazine and carbaryl pesticide residues in vegetable samplesusing a multianalyte dipstick immunoassay format. | Food Addit Contam | 2003 Aug | 13129787 |
| Use of gas liquid chromatography/mass spectrometry for triazine herbicideresidues analysis in forage and milk. | Z Lebensm Unters Forsch | 1987 Aug | 3660950 |
Targets
- General Function:
- Transmembrane signaling receptor activity
- Specific Function:
- Cell-surface glycoprotein having a role in immunoadhesion. Mediates in the adhesion of blood neutrophils in cytokine-activated endothelium through interaction with PSGL1/SELPLG. May have a role in capillary morphogenesis.
- Gene Name:
- SELE
- Uniprot ID:
- P16581
- Molecular Weight:
- 66654.575 Da
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 ]
- General Function:
- Metal ion binding
- Specific Function:
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
- Gene Name:
- PDE4A
- Uniprot ID:
- P27815
- Molecular Weight:
- 98142.155 Da
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 ]
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 Da
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 ]
- General Function:
- Virus receptor activity
- Specific Function:
- ICAM proteins are ligands for the leukocyte adhesion protein LFA-1 (integrin alpha-L/beta-2). During leukocyte trans-endothelial migration, ICAM1 engagement promotes the assembly of endothelial apical cups through ARHGEF26/SGEF and RHOG activation.(Microbial infection) Acts as a receptor for major receptor group rhinovirus A-B capsid proteins (PubMed:1968231, PubMed:2538243). Acts as a receptor for Coxsackievirus A21 capsid proteins (PubMed:11160747, PubMed:16004874, PubMed:9539703). Upon Kaposi's sarcoma-associated herpesvirus/HHV-8 infection, is degraded by viral E3 ubiquitin ligase MIR2, presumably to prevent lysis of infected cells by cytotoxic T-lymphocytes and NK cell (PubMed:11413168).
- Gene Name:
- ICAM1
- Uniprot ID:
- P05362
- Molecular Weight:
- 57824.785 Da
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 ]
- 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
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 ]
- 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
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 ]
- 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
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 ]
- General Function:
- Steroid binding
- Specific Function:
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
- Gene Name:
- UGT1A1
- Uniprot ID:
- P22309
- Molecular Weight:
- 59590.91 Da
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 ]
- 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
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 ]
- 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
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 ]
- General Function:
- Tumor necrosis factor receptor binding
- Specific Function:
- Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation. Impairs regulatory T-cells (Treg) function in individuals with rheumatoid arthritis via FOXP3 dephosphorylation. Upregulates the expression of protein phosphatase 1 (PP1), which dephosphorylates the key 'Ser-418' residue of FOXP3, thereby inactivating FOXP3 and rendering Treg cells functionally defective (PubMed:23396208). Key mediator of cell death in the anticancer action of BCG-stimulated neutrophils in combination with DIABLO/SMAC mimetic in the RT4v6 bladder cancer cell line (PubMed:22517918).The TNF intracellular domain (ICD) form induces IL12 production in dendritic cells.
- Gene Name:
- TNF
- Uniprot ID:
- P01375
- Molecular Weight:
- 25644.15 Da
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 ]