Metosulam
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Basic Info
| Common Name | Metosulam(F06309) |
| 2D Structure | |
| FRCD ID | F06309 |
| CAS Number | 139528-85-1 |
| PubChem CID | 86422 |
| Formula | C14H13Cl2N5O4S |
| IUPAC Name | N-(2,6-dichloro-3-methylphenyl)-5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide |
| InChI Key | VGHPMIFEKOFHHQ-UHFFFAOYSA-N |
| InChI | InChI=1S/C14H13Cl2N5O4S/c1-7-4-5-8(15)12(11(7)16)20-26(22,23)14-18-13-17-9(24-2)6-10(25-3)21(13)19-14/h4-6,20H,1-3H3 |
| Canonical SMILES | CC1=C(C(=C(C=C1)Cl)NS(=O)(=O)C2=NN3C(=CC(=NC3=N2)OC)OC)Cl |
| Isomeric SMILES | CC1=C(C(=C(C=C1)Cl)NS(=O)(=O)C2=NN3C(=CC(=NC3=N2)OC)OC)Cl |
| Synonyms |
N-(2,6-Dichloro-3-methylphenyl)-5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide
Metosulam
139528-85-1
Metosulam [ISO]
UNII-38SY84A64X
CHEBI:82024
38SY84A64X
AC1L3BIE
SCHEMBL55076
CHEMBL2288020
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Triazolopyrimidines |
| Subclass | 1,2,4-triazolopyrimidine-2-sulfonamides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 1,2,4-triazolopyrimidine-2-sulfonanilides |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | 1,2,4-triazolopyrimidine-2-sulfonanilide - Sulfanilide - 1,3-dichlorobenzene - Alkyl aryl ether - Chlorobenzene - Halobenzene - Toluene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Pyrimidine - Organosulfonic acid amide - Azole - Heteroaromatic compound - Aminosulfonyl compound - 1,2,4-triazole - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Triazole - Sulfonyl - Azacycle - Ether - Organonitrogen compound - Organochloride - Organohalogen compound - Organooxygen compound - Organosulfur compound - Organic oxygen compound - Organopnictogen compound - Organic nitrogen compound - Organic oxide - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as 1,2,4-triazolopyrimidine-2-sulfonanilides. These are polycyclic aromatic compounds containing a 1,2,4-triazolo[1,5-a]pyrimidine ring system, which is substituted with a sulfonanilide at the 2-position. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 418.249 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 5 |
| Complexity | 594 |
| Monoisotopic Mass | 417.007 |
| Exact Mass | 417.007 |
| XLogP | 3.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 26 |
| 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- | 0.7761 |
| Human Intestinal Absorption | HIA+ | 0.9455 |
| Caco-2 Permeability | Caco2- | 0.5129 |
| P-glycoprotein Substrate | Non-substrate | 0.8158 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7774 |
| Non-inhibitor | 0.8960 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8568 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.4294 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6363 |
| CYP450 2D6 Substrate | Non-substrate | 0.8266 |
| CYP450 3A4 Substrate | Non-substrate | 0.5156 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7190 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5553 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8860 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5371 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.5644 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7364 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9125 |
| Non-inhibitor | 0.7833 | |
| AMES Toxicity | Non AMES toxic | 0.6884 |
| Carcinogens | Non-carcinogens | 0.6371 |
| Fish Toxicity | High FHMT | 0.9957 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9008 |
| Honey Bee Toxicity | Low HBT | 0.8313 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.6699 |
| Carcinogenicity (Three-class) | Non-required | 0.6062 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.9303 | LogS |
| Caco-2 Permeability | 1.1003 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1473 | LD50, mol/kg |
| Fish Toxicity | 1.5464 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6584 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Onions ('Cipollotto Nocerino PDO', Pearl onions, Rakkyo/Chinese onions, Silverskin onions/pickled onions,) | 0220020 | European Union | 0.01* | 09/08/2016 | |
| Tomatoes (Alkekengi/Chinese lanterns/ground cherries, Cape gooseberries, Cherry tomatoes, Dwarf Cape gooseberries/strawberry tomatoes, Gojiberries/wolfberries, Gojiberries/wolfberries, Litchi tomat... | 0231010 | European Union | 0.01* | 09/08/2016 | |
| Brassica vegetables (excluding brassica roots and brassica baby leaf crops) | 0240000 | European Union | 0.01* | 09/08/2016 | |
| Chinese cabbages/pe-tsai (Chinese flat cabbages/tatsoi/tai goo choi, Indian mustards/mustard greens, Komatsuna/mustard spinaches, Mizuna (4), Pak-choi/paksoi, Turnip greens/turnip tops (5), Seakale,) | 0243010 | European Union | 0.01* | 09/08/2016 | |
| 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 | 0.02* | 09/08/2016 | |
| Laurel/bay leaves (Curry leaves, Kaffir lime leaves, Siamese cassia, Wild betel leaves, Pandan leaves,) | 0256090 | European Union | 0.02* | 09/08/2016 | |
| Tarragon (Aztec sweet herb, Epazote/Mexican tea/wormseed, Hyssop, Lemongrass, Mexican oregano, Nettle, Other species of the genus Urtica, not elsewhere mentioned, Russian tarragon, Stevia,) | 0256100 | European Union | 0.02* | 09/08/2016 | |
| Beans (with pods) (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, ... | 0260010 | European Union | 0.01* | 09/08/2016 | |
| Borage seeds (Corn gromwell seeds, Evening primrose seeds, Honesty seeds, Honesty seeds, Perilla seeds, Purple viper's bugloss seeds,) | 0401120 | European Union | 0.01* | 09/08/2016 | |
| Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei... | 0631030 | European Union | 0.05* | 09/08/2016 | |
| Others (2) | 0810990 | European Union | 0.05* | 09/08/2016 | |
| Shallots (French grey shallots, Persian shallots,) | 0220030 | European Union | 0.01* | 09/08/2016 | |
| Spring onions/green onions and Welsh onions (Tree onions/Egyptian walking onions, Green garlic,) | 0220040 | European Union | 0.01* | 09/08/2016 | |
| Others (2) | 0220990 | European Union | 0.01* | 09/08/2016 | |
| Fruiting vegetables | 0230000 | European Union | 0.01* | 09/08/2016 | |
| (a) Solanaceae and Malvaceae | 0231000 | European Union | 0.01* | 09/08/2016 | |
| Sweet peppers/bell peppers (Chili peppers,) | 0231020 | European Union | 0.01* | 09/08/2016 | |
| Aubergines/eggplants (Antroewas/African eggplants/gboma, Ethiopian eggplants/gilo', Pepinos, Thorn apples, Turkey berries/devil's figs/pea eggplants/pea aubergines, Kangaroo apples/poroporo,) | 0231030 | European Union | 0.01* | 09/08/2016 | |
| Okra/lady's fingers | 0231040 | European Union | 0.01* | 09/08/2016 | |
| Others (2) | 0231990 | European Union | 0.01* | 09/08/2016 |