Phenmedipham
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Basic Info
| Common Name | Phenmedipham(F04018) |
| 2D Structure | |
| Description | Phenmedipham is a selective herbicide of the carbanilate and biscarbamate classes. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. Phenmedipham was developed by Schering AG and approved for use in the United States in 1970. Today, about 100 tons of Phenmedipham are used each year. It is commonly used in beet, spinach, and strawberry crops to protect against weeds, often in comination with Desmedipham under the trade names Betanal or Betamax. (L795) |
| FRCD ID | F04018 |
| CAS Number | 13684-63-4 |
| PubChem CID | 24744 |
| Formula | C16H16N2O4 |
| IUPAC Name | [3-(methoxycarbonylamino)phenyl] N-(3-methylphenyl)carbamate |
| InChI Key | IDOWTHOLJBTAFI-UHFFFAOYSA-N |
| InChI | InChI=1S/C16H16N2O4/c1-11-5-3-6-12(9-11)18-16(20)22-14-8-4-7-13(10-14)17-15(19)21-2/h3-10H,1-2H3,(H,17,19)(H,18,20) |
| Canonical SMILES | CC1=CC(=CC=C1)NC(=O)OC2=CC=CC(=C2)NC(=O)OC |
| Isomeric SMILES | CC1=CC(=CC=C1)NC(=O)OC2=CC=CC(=C2)NC(=O)OC |
| Synonyms |
Phenmedipham
13684-63-4
3-((Methoxycarbonyl)amino)phenyl m-tolylcarbamate
Fenmedifam
BETANAL
Phenmediphame
Kemifam
Spin-aid
Synbetan P
Schering 4072
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Phenylcarbamic acid esters |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenylcarbamic acid esters |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenylcarbamic acid ester - Phenoxy compound - Toluene - Carbamic acid ester - Carbonic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 300.314 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 5 |
| Complexity | 388 |
| Monoisotopic Mass | 300.111 |
| Exact Mass | 300.111 |
| XLogP | 3.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| 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+ | 0.8498 |
| Human Intestinal Absorption | HIA+ | 0.9173 |
| Caco-2 Permeability | Caco2+ | 0.5228 |
| P-glycoprotein Substrate | Non-substrate | 0.7512 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7802 |
| Non-inhibitor | 0.6480 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9254 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8545 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7451 |
| CYP450 2D6 Substrate | Non-substrate | 0.6588 |
| CYP450 3A4 Substrate | Substrate | 0.5061 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6217 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8038 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9451 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8394 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7227 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6189 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9522 |
| Non-inhibitor | 0.8893 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Non-carcinogens | 0.7815 |
| Fish Toxicity | High FHMT | 0.9873 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9883 |
| Honey Bee Toxicity | Low HBT | 0.5524 |
| Biodegradation | Not ready biodegradable | 0.9699 |
| Acute Oral Toxicity | III | 0.7677 |
| Carcinogenicity (Three-class) | Non-required | 0.4249 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.7371 | LogS |
| Caco-2 Permeability | 0.8558 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9071 | LD50, mol/kg |
| Fish Toxicity | 0.3497 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7903 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Horseradishes (Dandelion roots, Gentiana roots, East Indian galangal/aromatic ginger/sand galangal, Fingerroot, Galangal roots, Galangal roots, Galangal roots, Galangal roots, Ginger roots, Greater... | 0213040 | European Union | 0.01* | 09/06/2016 | |
| Parsley (Root parsley leaves,) | 0256040 | European Union | 7 | 09/06/2016 | |
| Sage (Borage, Curry herb, Greek sage, Jamé's sage/Mexican sage, Other species and hybrids of genus Salvia, not elsewhere mentioned,) | 0256050 | European Union | 7 | 09/06/2016 | |
| Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L... | 0256080 | European Union | 7 | 09/06/2016 | |
| Linseeds | 0401010 | European Union | 0.01* | 09/06/2016 | |
| Rapeseeds/canola seeds (Radish seeds, Turnip rape seeds,) | 0401060 | European Union | 0.01* | 09/06/2016 | |
| Common millet/proso millet (Black fonio, Canary grass, Finger millet/African millet/koracan, Foxtail millet, Job's tears, Little millet, Pearl millet, Teff/tef, White fonio,) | 0500040 | European Union | 0.01* | 09/06/2016 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 09/06/2016 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 09/06/2016 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 09/06/2016 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 09/06/2016 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 09/06/2016 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.01* | 09/06/2016 | |
| Others (2) | 0110990 | European Union | 0.01* | 09/06/2016 | |
| Tree nuts | 0120000 | European Union | 0.01* | 09/06/2016 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.01* | 09/06/2016 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 09/06/2016 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 09/06/2016 | |
| Chestnuts | 0120040 | European Union | 0.01* | 09/06/2016 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 09/06/2016 |
Targets
- General Function:
- Fatty acid amide hydrolase activity
- Specific Function:
- Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes polyunsaturated substrate anandamide preferentially as compared to monounsaturated substrates.
- Gene Name:
- FAAH
- Uniprot ID:
- O00519
- Molecular Weight:
- 63065.28 Da
References
- Vincent F, Nguyen MT, Emerling DE, Kelly MG, Duncton MA: Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors. Bioorg Med Chem Lett. 2009 Dec 1;19(23):6793-6. doi: 10.1016/j.bmcl.2009.09.086. Epub 2009 Sep 30. [19850474 ]
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
References
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
- General Function:
- Identical protein binding
- Specific Function:
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name:
- BCHE
- Uniprot ID:
- P06276
- Molecular Weight:
- 68417.575 Da
- Mechanism of Action:
- Like the organophosphates, their mode of action is inhibition of cholinesterase enzymes, affecting nerve impulse transmission.
References
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 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 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
- 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 ]