Asulam
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Basic Info
| Common Name | Asulam(F03957) |
| 2D Structure | |
| Description | 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. (L795) |
| FRCD ID | F03957 |
| CAS Number | 3337-71-1 |
| PubChem CID | 18752 |
| Formula | C8H10N2O4S |
| IUPAC Name | methyl N-(4-aminophenyl)sulfonylcarbamate |
| InChI Key | VGPYEHKOIGNJKV-UHFFFAOYSA-N |
| InChI | InChI=1S/C8H10N2O4S/c1-14-8(11)10-15(12,13)7-4-2-6(9)3-5-7/h2-5H,9H2,1H3,(H,10,11) |
| Canonical SMILES | COC(=O)NS(=O)(=O)C1=CC=C(C=C1)N |
| Isomeric SMILES | COC(=O)NS(=O)(=O)C1=CC=C(C=C1)N |
| Synonyms |
Methyl sulfanilylcarbamate
ASULAM
3337-71-1
Asilan
Asulox
Jonnix
Asulox F
Plakin
Asulox 40
Methyl sulphanilylcarbamate
|
| 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 | Aminobenzenesulfonamides |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Aminobenzenesulfonamide - Benzenesulfonyl group - Aniline or substituted anilines - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Aminosulfonyl compound - Carbonic acid derivative - Carbonyl group - Organic nitrogen compound - Amine - Primary amine - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organopnictogen compound - Organic oxide - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 230.238 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Complexity | 314 |
| Monoisotopic Mass | 230.036 |
| Exact Mass | 230.036 |
| XLogP | -0.3 |
| 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+ | 0.9541 |
| Human Intestinal Absorption | HIA+ | 0.9297 |
| Caco-2 Permeability | Caco2- | 0.5904 |
| P-glycoprotein Substrate | Non-substrate | 0.8798 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9588 |
| Non-inhibitor | 0.8867 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9513 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5554 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6719 |
| CYP450 2D6 Substrate | Non-substrate | 0.8730 |
| CYP450 3A4 Substrate | Non-substrate | 0.7436 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8979 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.5392 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9302 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5000 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9425 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8582 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9927 |
| Non-inhibitor | 0.9662 | |
| AMES Toxicity | Non AMES toxic | 0.7662 |
| Carcinogens | Non-carcinogens | 0.8368 |
| Fish Toxicity | High FHMT | 0.9341 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.5060 |
| Honey Bee Toxicity | Low HBT | 0.6725 |
| Biodegradation | Not ready biodegradable | 0.9974 |
| Acute Oral Toxicity | III | 0.7853 |
| Carcinogenicity (Three-class) | Non-required | 0.5760 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.7223 | LogS |
| Caco-2 Permeability | 0.5768 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0922 | LD50, mol/kg |
| Fish Toxicity | 1.8777 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.0090 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Blackberries | 0153010 | European Union | 0.05* | 13/05/2015 | |
| Citrus fruits | 0110000 | European Union | 0.05* | 13/05/2015 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.05* | 13/05/2015 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.05* | 13/05/2015 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.05* | 13/05/2015 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.05* | 13/05/2015 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.05* | 13/05/2015 | |
| Others (2) | 0110990 | European Union | 0.05* | 13/05/2015 | |
| Tree nuts | 0120000 | European Union | 0.1* | 13/05/2015 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.1* | 13/05/2015 | |
| Brazil nuts | 0120020 | European Union | 0.1* | 13/05/2015 | |
| Cashew nuts | 0120030 | European Union | 0.1* | 13/05/2015 | |
| Chestnuts | 0120040 | European Union | 0.1* | 13/05/2015 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.1* | 13/05/2015 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.1* | 13/05/2015 | |
| Macadamias | 0120070 | European Union | 0.1* | 13/05/2015 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.1* | 13/05/2015 | |
| Pistachios | 0120100 | European Union | 0.1* | 13/05/2015 | |
| Walnuts | 0120110 | European Union | 0.1* | 13/05/2015 | |
| Others (2) | 0120990 | European Union | 0.1* | 13/05/2015 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Crops with target-site herbicide resistance for Orobanche and Striga control. | Pest Manag Sci | 2009 May | 19280593 |
| Validation of a fast and easy method for the determination of residues from 229pesticides in fruits and vegetables using gas and liquid chromatography and mass spectrometric detection. | J AOAC Int | 2005 Mar-Apr | 15859089 |
| The effects of a pesticide mixture on aquatic ecosystems differing in trophicstatus: responses of the macrophyte Myriophyllum spicatum and the periphyticalgal community. | Ecotoxicol Environ Saf | 2004 Mar | 15041261 |
| Aquatic risk assessment of a realistic exposure to pesticides used in bulb crops: a microcosm study. | Environ Toxicol Chem | 2004 Jun | 15376534 |
| Contamination of honey by the herbicide asulam and its antibacterial activemetabolite sulfanilamide. | Food Addit Contam | 2004 Jun | 15204534 |
Targets
- 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:
- 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 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:
- Xenobiotic-transporting atpase activity
- Specific Function:
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. Implicated in the efflux of numerous drugs and xenobiotics: mitoxantrone, the photosensitizer pheophorbide, camptothecin, methotrexate, azidothymidine (AZT), and the anthracyclines daunorubicin and doxorubicin.
- Gene Name:
- ABCG2
- Uniprot ID:
- Q9UNQ0
- Molecular Weight:
- 72313.47 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 ]