Penoxsulam
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Basic Info
| Common Name | Penoxsulam(F05118) |
| 2D Structure | |
| Description | Penoxsulam, also sold under the brand name Granite, is an acetolactate synthase inhibitor herbicide developed in the mid-2000s. This substance is designed to control existing broadleaf weeds and similar plants in lawns, rice fields and cereal crops. |
| FRCD ID | F05118 |
| CAS Number | 219714-96-2 |
| PubChem CID | 11784975 |
| Formula | C16H14F5N5O5S |
| IUPAC Name | 2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide |
| InChI Key | SYJGKVOENHZYMQ-UHFFFAOYSA-N |
| InChI | InChI=1S/C16H14F5N5O5S/c1-29-10-6-22-15(30-2)26-13(10)23-14(24-26)25-32(27,28)12-8(16(19,20)21)4-3-5-9(12)31-7-11(17)18/h3-6,11H,7H2,1-2H3,(H,24,25) |
| Canonical SMILES | COC1=CN=C(N2C1=NC(=N2)NS(=O)(=O)C3=C(C=CC=C3OCC(F)F)C(F)(F)F)OC |
| Isomeric SMILES | COC1=CN=C(N2C1=NC(=N2)NS(=O)(=O)C3=C(C=CC=C3OCC(F)F)C(F)(F)F)OC |
| Synonyms |
Penoxsulam
2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide
219714-96-2
Granite
Penoxsulam [ISO]
UNII-784ELC1SCZ
784ELC1SCZ
CHEBI:81776
2-(2,2-difluoroethoxy)-n-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide
PXD
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzenesulfonamides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzenesulfonamides |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Benzenesulfonamide - Trifluoromethylbenzene - Benzenesulfonyl group - Triazolopyrimidine - Phenoxy compound - Phenol ether - Alkyl aryl ether - Pyrimidine - Organosulfonic acid amide - Azole - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Triazole - 1,2,4-triazole - Heteroaromatic compound - Aminosulfonyl compound - Ether - Organoheterocyclic compound - Azacycle - Alkyl halide - Alkyl fluoride - Organic oxide - Organopnictogen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organofluoride - Hydrocarbon derivative - Organic nitrogen compound - Organic oxygen compound - Organohalogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 483.37 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 14 |
| Rotatable Bond Count | 8 |
| Complexity | 727 |
| Monoisotopic Mass | 483.064 |
| Exact Mass | 483.064 |
| XLogP | 2.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 32 |
| 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+ | 0.5000 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2- | 0.5250 |
| P-glycoprotein Substrate | Non-substrate | 0.7988 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7133 |
| Non-inhibitor | 0.5696 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8097 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.3854 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.5875 |
| CYP450 2D6 Substrate | Non-substrate | 0.8200 |
| CYP450 3A4 Substrate | Non-substrate | 0.5133 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5834 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5687 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8762 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5000 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7454 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6225 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9179 |
| Non-inhibitor | 0.7134 | |
| AMES Toxicity | Non AMES toxic | 0.6334 |
| Carcinogens | Non-carcinogens | 0.6581 |
| Fish Toxicity | High FHMT | 0.9192 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8866 |
| Honey Bee Toxicity | Low HBT | 0.8137 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.6222 |
| Carcinogenicity (Three-class) | Non-required | 0.6010 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.8151 | LogS |
| Caco-2 Permeability | 1.2146 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4196 | LD50, mol/kg |
| Fish Toxicity | 1.4443 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5528 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Rice(Brown Rice) | Japan | 0.02ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Environmental and human health risk indicators for agricultural pesticides inestuaries. | Ecotoxicol Environ Saf | 2018 Apr 15 | 29288903 |
| Multiple-herbicide resistance in Echinochloa crus-galli var. formosensis, anallohexaploid weed species, in dry-seeded rice. | Pestic Biochem Physiol | 2015 Mar | 25868810 |
| Physiological and molecular basis of acetolactate synthase-inhibiting herbicideresistance in barnyardgrass (Echinochloa crus-galli). | J Agric Food Chem | 2013 Jan 16 | 23237199 |
| Mechanism of resistance to penoxsulam in late watergrass [ Echinochloaphyllopogon (Stapf) Koss.]. | J Agric Food Chem | 2009 May 13 | 19323496 |
| Penoxsulam--structure-activity relationships of triazolopyrimidine sulfonamides. | Bioorg Med Chem | 2009 Jun 15 | 19464188 |
| Cross-resistance to herbicides of five ALS-inhibiting groups and sequencing ofthe ALS gene in Cyperus difformis L. | J Agric Food Chem | 2009 Feb 25 | 19191488 |
| Microbial degradation of penoxsulam in flooded rice field soils. | J Agric Food Chem | 2006 Aug 9 | 16881702 |
| Partitioning of penoxsulam, a new sulfonamide herbicide. | J Agric Food Chem | 2005 Sep 7 | 16131127 |
Targets
- General Function:
- Transmembrane signaling receptor activity
- Specific Function:
- Involved in lymphocyte proliferation and functions as a signal transmitting receptor in lymphocytes, natural killer (NK) cells, and platelets.
- Gene Name:
- CD69
- Uniprot ID:
- Q07108
- Molecular Weight:
- 22559.25 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:
- Zinc ion binding
- Specific Function:
- Cleaves collagens of types I, II, and III at one site in the helical domain. Also cleaves collagens of types VII and X. In case of HIV infection, interacts and cleaves the secreted viral Tat protein, leading to a decrease in neuronal Tat's mediated neurotoxicity.
- Gene Name:
- MMP1
- Uniprot ID:
- P03956
- Molecular Weight:
- 54006.61 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:
- 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:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 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 ]