Fenamidone
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Basic Info
| Common Name | Fenamidone(F05065) |
| 2D Structure | |
| Description | Fenamidone is a foliar fungicide used on grapes, ornamentals, potatoes, tobacco, and vegetables. It exerts its fungicidal effects by acting as a Qo inhibitor. |
| FRCD ID | F05065 |
| CAS Number | 161326-34-7 |
| PubChem CID | 10403199 |
| Formula | C17H17N3OS |
| IUPAC Name | (5S)-3-anilino-5-methyl-2-methylsulfanyl-5-phenylimidazol-4-one |
| InChI Key | LMVPQMGRYSRMIW-KRWDZBQOSA-N |
| InChI | InChI=1S/C17H17N3OS/c1-17(13-9-5-3-6-10-13)15(21)20(16(18-17)22-2)19-14-11-7-4-8-12-14/h3-12,19H,1-2H3/t17-/m0/s1 |
| Canonical SMILES | CC1(C(=O)N(C(=N1)SC)NC2=CC=CC=C2)C3=CC=CC=C3 |
| Isomeric SMILES | C[C@@]1(C(=O)N(C(=N1)SC)NC2=CC=CC=C2)C3=CC=CC=C3 |
| Synonyms |
(5S)-3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)-4H-imidazol-4-one
Fenamidone
161326-34-7
Fenamidone [ISO]
Consento
UNII-DN24MG2Z5E
DN24MG2Z5E
(S)-1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one
CHEBI:83258
1-Anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives |
| Direct Parent | Alpha amino acids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Alpha-amino acid or derivatives - Phenylhydrazine - Monocyclic benzene moiety - Imidazolinone - Benzenoid - 2-imidazoline - Carboxylic acid hydrazide - Azacycle - Sulfenyl compound - Organoheterocyclic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organic nitrogen compound - Organic oxygen compound - Carbonyl group - Organopnictogen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 311.403 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Complexity | 441 |
| Monoisotopic Mass | 311.109 |
| Exact Mass | 311.109 |
| XLogP | 4.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| Defined Atom Stereocenter Count | 1 |
| 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+ | 0.8758 |
| Human Intestinal Absorption | HIA+ | 0.9443 |
| Caco-2 Permeability | Caco2+ | 0.5310 |
| P-glycoprotein Substrate | Non-substrate | 0.7664 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6075 |
| Non-inhibitor | 0.8431 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7887 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6790 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6473 |
| CYP450 2D6 Substrate | Non-substrate | 0.8360 |
| CYP450 3A4 Substrate | Substrate | 0.5686 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5207 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.6907 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8863 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5942 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7032 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8580 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9848 |
| Non-inhibitor | 0.7026 | |
| AMES Toxicity | Non AMES toxic | 0.6386 |
| Carcinogens | Non-carcinogens | 0.7723 |
| Fish Toxicity | High FHMT | 0.9986 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9335 |
| Honey Bee Toxicity | Low HBT | 0.8321 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7719 |
| Carcinogenicity (Three-class) | Non-required | 0.4401 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.2678 | LogS |
| Caco-2 Permeability | 1.1070 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2175 | LD50, mol/kg |
| Fish Toxicity | 1.4887 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6121 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Other Flowering Brassicas | Britain | 0.02mg/kg | |||
| Other Small Fruit & Berries (Other Than Wild) | Britain | 0.02mg/kg | |||
| Maize | Britain | 0.02mg/kg | |||
| Other Potatoes | Japan | 0.02ppm | |||
| Sesame Seeds | Korea | 0.2ppm | |||
| Quail | 1030040 | European Union | 0.01* | 26/06/2018 | |
| Honey and other apiculture products (7) | 1040000 | European Union | 0.05* | 26/06/2018 | |
| Amphibians and Reptiles (Crocodiles, Frog legs, Snakes, Turtles, Other Amphibians and Reptiles, Other frog legs from frogs not belonging to the genus Rana,) | 1050000 | European Union | 0.01* | 26/06/2018 | |
| Terrestrial invertebrate animals (Earthworms, Insects, Snails, Other terrestrial invertebrate animals, Other edible snails not belonging to the genus Helix,) | 1060000 | European Union | 0.01* | 26/06/2018 | |
| Wild terrestrial vertebrate animals (Feathered wild game, Furred wild game, Kangaroos,) | 1070000 | European Union | 0.01* | 26/06/2018 | |
| Geese | 1030030 | European Union | 0.01* | 26/06/2018 | |
| Others (2) (Emu, Nandu/greater rhea, Ostrich, Other eggs producer birds,) | 1030990 | European Union | 0.01* | 26/06/2018 | |
| Other Head Brassicas | Britain | 0.02mg/kg | |||
| Head Cabbage | Britain | 0.02mg/kg | |||
| Brussels Sprouts | Britain | 0.02mg/kg | |||
| Cauliflower | Britain | 0.02mg/kg | |||
| Broccoli | Britain | 0.02mg/kg | |||
| Sweet Corn | Britain | 0.02mg/kg | |||
| Other Cucurbits-Inedible Peel | Britain | 0.02mg/kg | |||
| Watermelons | Britain | 0.02mg/kg |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Dynamics and residues of mixed formulation of fenamidone and mancozeb in gherkin field ecosystem. | Ecotoxicol Environ Saf | 2013 Dec | 24041529 |
| Influence of fenamidone, indoxacarb, pyraclostrobin, and deltamethrin on thepopulation of natural yeast microflora during winemaking of two sardinian grapecultivars. | J Environ Sci Health B | 2011 | 21726147 |
| Residue-free wines: fate of some quinone outside inhibitor (QoI) fungicides inthe winemaking process. | J Agric Food Chem | 2009 Mar 25 | 19292467 |
| Multiresidue determination of 11 new fungicides in grapes and wines byliquid-liquid extraction/clean-up and programmable temperature vaporizationinjection with analyte protectants/gas chromatography/ion trap mass spectrometry. | J Chromatogr A | 2009 Aug 7 | 19576591 |
| Chemical control of downy mildew on lettuce and basil under greenhouse. | Commun Agric Appl Biol Sci | 2009 | 20222581 |
Targets
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 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:
- Sulfotransferase activity
- Specific Function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
- Gene Name:
- SULT2A1
- Uniprot ID:
- Q06520
- Molecular Weight:
- 33779.57 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:
- Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
- Specific Function:
- Nuclear phosphoprotein which forms a tight but non-covalently linked complex with the JUN/AP-1 transcription factor. In the heterodimer, FOS and JUN/AP-1 basic regions each seems to interact with symmetrical DNA half sites. On TGF-beta activation, forms a multimeric SMAD3/SMAD4/JUN/FOS complex at the AP1/SMAD-binding site to regulate TGF-beta-mediated signaling. Has a critical function in regulating the development of cells destined to form and maintain the skeleton. It is thought to have an important role in signal transduction, cell proliferation and differentiation. In growing cells, activates phospholipid synthesis, possibly by activating CDS1 and PI4K2A. This activity requires Tyr-dephosphorylation and association with the endoplasmic reticulum.
- Gene Name:
- FOS
- Uniprot ID:
- P01100
- Molecular Weight:
- 40694.855 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:
- Transferase activity
- Specific Function:
- Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
- Gene Name:
- CD38
- Uniprot ID:
- P28907
- Molecular Weight:
- 34328.145 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:
- 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:
- Interleukin-8 receptor binding
- Specific Function:
- IL-8 is a chemotactic factor that attracts neutrophils, basophils, and T-cells, but not monocytes. It is also involved in neutrophil activation. It is released from several cell types in response to an inflammatory stimulus. IL-8(6-77) has a 5-10-fold higher activity on neutrophil activation, IL-8(5-77) has increased activity on neutrophil activation and IL-8(7-77) has a higher affinity to receptors CXCR1 and CXCR2 as compared to IL-8(1-77), respectively.
- Gene Name:
- CXCL8
- Uniprot ID:
- P10145
- Molecular Weight:
- 11097.98 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:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor for TNFSF5/CD40LG. Transduces TRAF6- and MAP3K8-mediated signals that activate ERK in macrophages and B cells, leading to induction of immunoglobulin secretion.
- Gene Name:
- CD40
- Uniprot ID:
- P25942
- Molecular Weight:
- 30618.76 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:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 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:
- Transcriptional activator activity, rna polymerase ii distal enhancer sequence-specific binding
- Specific Function:
- Transcription activator that binds to antioxidant response (ARE) elements in the promoter regions of target genes. Important for the coordinated up-regulation of genes in response to oxidative stress. May be involved in the transcriptional activation of genes of the beta-globin cluster by mediating enhancer activity of hypersensitive site 2 of the beta-globin locus control region.
- Gene Name:
- NFE2L2
- Uniprot ID:
- Q16236
- Molecular Weight:
- 67825.9 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:
- Receptor signaling protein serine/threonine kinase activity
- Specific Function:
- On ligand binding, forms a receptor complex consisting of two type II and two type I transmembrane serine/threonine kinases. Type II receptors phosphorylate and activate type I receptors which autophosphorylate, then bind and activate SMAD transcriptional regulators. Binds to BMP-7, BMP-2 and, less efficiently, BMP-4. Binding is weak but enhanced by the presence of type I receptors for BMPs.
- Gene Name:
- BMPR2
- Uniprot ID:
- Q13873
- Molecular Weight:
- 115200.475 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:
- Hydroxymethylglutaryl-coa synthase activity
- Specific Function:
- This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
- Gene Name:
- HMGCS2
- Uniprot ID:
- P54868
- Molecular Weight:
- 56634.915 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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 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:
- Protease binding
- Specific Function:
- Initiates blood coagulation by forming a complex with circulating factor VII or VIIa. The [TF:VIIa] complex activates factors IX or X by specific limited protolysis. TF plays a role in normal hemostasis by initiating the cell-surface assembly and propagation of the coagulation protease cascade.
- Gene Name:
- F3
- Uniprot ID:
- P13726
- Molecular Weight:
- 33067.3 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 ]