Mecarbinzid
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Basic Info
| Common Name | Mecarbinzid(F04006) |
| 2D Structure | |
| Description | Mecarbinzid is a systemic benzimidazole fungicide that is selectively toxic to microorganisms and invertebrates, especially earthworms. It is not widely used anymore due to widespread fungal resistance. The in vitro antifungal activity of benzimidazole compounds was first observed in 1944. Some of the benzimidazole derivatives which have been exploited for commercial use as agricultural pesticides are carbendazim, benomyl, mecarbinzid, debacarb, fuberidazole, and rabenzazole. Of these, carbendazim, benomyl, debacarb and mecarbinzid are benzimidazole-2-carbamates. benzimidazol-2-yl carbamates like Mecarbinzid bind to microtubules, interfering with cell functions, such as meiosis and intracellular transportation. Due to the widespread use of these fungicidal agents and their specific action, resistance is common in many fungal species. For instance, strains of Botrytis which cause gray mold in ornamental crops are now largely resistant to methyl benzimidazole carbamate fungicides. Solubility problems of these compounds have contributed to their low bioavailability which has restricted their use in the treatment of fungal diseases in plants and have now lost effectiveness for many important diseases. |
| FRCD ID | F04006 |
| CAS Number | 27386-64-7 |
| PubChem CID | 20055210 |
| Formula | C13H16N4O3S |
| IUPAC Name | methyl N-[1-(2-methylsulfanylethylcarbamoyl)benzimidazol-2-yl]carbamate |
| InChI Key | ZCAHBOURBFRXOT-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H16N4O3S/c1-20-13(19)16-11-15-9-5-3-4-6-10(9)17(11)12(18)14-7-8-21-2/h3-6H,7-8H2,1-2H3,(H,14,18)(H,15,16,19) |
| Canonical SMILES | COC(=O)NC1=NC2=CC=CC=C2N1C(=O)NCCSC |
| Isomeric SMILES | COC(=O)NC1=NC2=CC=CC=C2N1C(=O)NCCSC |
| Synonyms |
DTXSID7058046
Mecarbinzid
UNII-WS1R812595
27386-64-7
WS1R812595
Mecarbinzid [ISO]
SCHEMBL159671
BAS-320-F
CHEBI:82083
ZCAHBOURBFRXOT-UHFFFAOYSA-N
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Benzimidazoles |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzimidazoles |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Benzimidazole - N-substituted imidazole - Benzenoid - Azole - Imidazole - Heteroaromatic compound - Isourea - Carboximidic acid derivative - Azacycle - Thioether - Sulfenyl compound - Dialkylthioether - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organic nitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds). |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 308.356 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Complexity | 382 |
| Monoisotopic Mass | 308.094 |
| Exact Mass | 308.094 |
| XLogP | 1.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 21 |
| 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+ | 0.7751 |
| Human Intestinal Absorption | HIA+ | 0.9968 |
| Caco-2 Permeability | Caco2- | 0.6144 |
| P-glycoprotein Substrate | Substrate | 0.6702 |
| P-glycoprotein Inhibitor | Inhibitor | 0.6446 |
| Non-inhibitor | 0.6330 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8293 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6028 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7417 |
| CYP450 2D6 Substrate | Non-substrate | 0.8004 |
| CYP450 3A4 Substrate | Non-substrate | 0.5122 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6316 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7212 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8634 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6015 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9374 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5707 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7874 |
| Inhibitor | 0.5354 | |
| AMES Toxicity | Non AMES toxic | 0.7733 |
| Carcinogens | Non-carcinogens | 0.8938 |
| Fish Toxicity | High FHMT | 0.9375 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8393 |
| Honey Bee Toxicity | Low HBT | 0.7128 |
| Biodegradation | Not ready biodegradable | 0.9906 |
| Acute Oral Toxicity | III | 0.5044 |
| Carcinogenicity (Three-class) | Non-required | 0.6455 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.0264 | LogS |
| Caco-2 Permeability | 0.7449 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9939 | LD50, mol/kg |
| Fish Toxicity | 1.4589 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4331 | pIGC50, ug/L |
Targets
- General Function:
- Ubiquitin protein ligase binding
- Specific Function:
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Gene Name:
- TUBB
- Uniprot ID:
- P07437
- Molecular Weight:
- 49670.515 Da
References
- Fujimura M, Oeda K, Inoue H, Kato T. "A single amino-acid substitution in the beta-tubulin gene of Neurospora confers both carbendazim resistance and diethofencarb sensitivity.". Curr Genet. 1992 Apr;21(4-5):399-404. [1388107 ]