Dimetan
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Basic Info
Common Name | Dimetan(F03989) |
2D Structure | |
Description | Dimetan is a carbamate pesticide. 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 | F03989 |
CAS Number | 122-15-6 |
PubChem CID | 31201 |
Formula | C11H17NO3 |
IUPAC Name | (5,5-dimethyl-3-oxocyclohexen-1-yl) N,N-dimethylcarbamate |
InChI Key | ITEQSCBLCCNACE-UHFFFAOYSA-N |
InChI | InChI=1S/C11H17NO3/c1-11(2)6-8(13)5-9(7-11)15-10(14)12(3)4/h5H,6-7H2,1-4H3 |
Canonical SMILES | CC1(CC(=CC(=O)C1)OC(=O)N(C)C)C |
Isomeric SMILES | CC1(CC(=CC(=O)C1)OC(=O)N(C)C)C |
Synonyms | 215ZV6RPXL DIMETAN Geigy 19258 UNII-215ZV6RPXL 122-15-6 EINECS 204-525-8 ENT 24,728 BRN 3280184 5,5-Dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate AI3-24728 |
Classifies | Pesticide |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic oxygen compounds |
Class | Organooxygen compounds |
Subclass | Carbonyl compounds |
Intermediate Tree Nodes | Ketones - Cyclic ketones |
Direct Parent | Cyclohexenones |
Alternative Parents | |
Molecular Framework | Aliphatic homomonocyclic compounds |
Substituents | Cyclohexenone - Carbamic acid ester - Enol ester - Carbonic acid derivative - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Aliphatic homomonocyclic compound |
Description | This compound belongs to the class of organic compounds known as cyclohexenones. These are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 211.261 |
Hydrogen Bond Donor Count | 0 |
Hydrogen Bond Acceptor Count | 3 |
Rotatable Bond Count | 2 |
Complexity | 316 |
Monoisotopic Mass | 211.121 |
Exact Mass | 211.121 |
XLogP | 1.2 |
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+ | 0.9381 |
Human Intestinal Absorption | HIA+ | 0.9974 |
Caco-2 Permeability | Caco2+ | 0.5802 |
P-glycoprotein Substrate | Non-substrate | 0.7384 |
P-glycoprotein Inhibitor | Inhibitor | 0.6016 |
Non-inhibitor | 0.9019 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9045 |
Distribution | ||
Subcellular localization | Mitochondria | 0.6960 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8270 |
CYP450 2D6 Substrate | Non-substrate | 0.8433 |
CYP450 3A4 Substrate | Substrate | 0.6386 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.8222 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.8580 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.8987 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.7861 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.8441 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8781 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9596 |
Non-inhibitor | 0.9731 | |
AMES Toxicity | Non AMES toxic | 0.6256 |
Carcinogens | Non-carcinogens | 0.6359 |
Fish Toxicity | High FHMT | 0.8083 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.8694 |
Honey Bee Toxicity | High HBT | 0.8107 |
Biodegradation | Not ready biodegradable | 0.9773 |
Acute Oral Toxicity | II | 0.7304 |
Carcinogenicity (Three-class) | Non-required | 0.5396 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -0.9123 | LogS |
Caco-2 Permeability | 1.4343 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 3.2143 | LD50, mol/kg |
Fish Toxicity | 1.1000 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.1744 | pIGC50, ug/L |
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