Imazapic
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Basic Info
| Common Name | Imazapic(F05087) |
| 2D Structure | |
| Description | Imazapic is a chemical used as an herbicide. It controls many broad leaf weeds and controls or suppresses some grasses in pasture, rangeland and certain types of turf. It has a half-life of around 120 days in soil. |
| FRCD ID | F05087 |
| CAS Number | 104098-48-8 |
| PubChem CID | 91770 |
| Formula | C14H17N3O3 |
| IUPAC Name | 5-methyl-2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)pyridine-3-carboxylic acid |
| InChI Key | PVSGXWMWNRGTKE-UHFFFAOYSA-N |
| InChI | InChI=1S/C14H17N3O3/c1-7(2)14(4)13(20)16-11(17-14)10-9(12(18)19)5-8(3)6-15-10/h5-7H,1-4H3,(H,18,19)(H,16,17,20) |
| Canonical SMILES | CC1=CN=C(C(=C1)C(=O)O)C2=NC(C(=O)N2)(C)C(C)C |
| Isomeric SMILES | CC1=CN=C(C(=C1)C(=O)O)C2=NC(C(=O)N2)(C)C(C)C |
| Synonyms |
Imazapic [ISO]
3-Pyridinecarboxylic acid, 2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl)-5-methyl-
Imazapic
Imazameth
104098-48-8
Imazamethapyr
Imazmethapyr
Cadre (trade name)
AC 263222
2-(4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-methylnicotinic acid
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives |
| Direct Parent | Alpha amino acids and derivatives |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Alpha-amino acid or derivatives - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Imidazolyl carboxylic acid derivative - Methylpyridine - Imidazolinone - Pyridine - 2-imidazoline - Heteroaromatic compound - Azacycle - Organoheterocyclic compound - Carboxylic acid amidine - Carboxylic acid - Monocarboxylic acid or derivatives - Amidine - Carboximidamide - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organonitrogen compound - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 275.308 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Complexity | 461 |
| Monoisotopic Mass | 275.127 |
| Exact Mass | 275.127 |
| XLogP | 1.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 20 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| 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- | 0.6229 |
| Human Intestinal Absorption | HIA+ | 0.9582 |
| Caco-2 Permeability | Caco2- | 0.6279 |
| P-glycoprotein Substrate | Non-substrate | 0.5558 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8591 |
| Non-inhibitor | 0.8893 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9339 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8260 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7218 |
| CYP450 2D6 Substrate | Non-substrate | 0.8034 |
| CYP450 3A4 Substrate | Non-substrate | 0.5992 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7158 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8385 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8960 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6392 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8637 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9072 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9990 |
| Non-inhibitor | 0.9453 | |
| AMES Toxicity | Non AMES toxic | 0.7821 |
| Carcinogens | Non-carcinogens | 0.7960 |
| Fish Toxicity | Low FHMT | 0.7042 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6573 |
| Honey Bee Toxicity | Low HBT | 0.8915 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7742 |
| Carcinogenicity (Three-class) | Non-required | 0.6417 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1688 | LogS |
| Caco-2 Permeability | 0.7048 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7100 | LD50, mol/kg |
| Fish Toxicity | 1.9793 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3928 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Kapok | 0402040 | European Union | 0.01* | 27/04/2017 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Synthesis optimization of oil palm empty fruit bunch and rice husk biochars forremoval of imazapic and imazapyr herbicides. | J Environ Manage | 2017 May 15 | 28226259 |
| Imazethapyr and imazapic, bispyribac-sodium and penoxsulam: zooplankton anddissipation in subtropical rice paddy water. | Sci Total Environ | 2015 May 1 | 25659307 |
| Analysis of the Photodegradation of the Imidazolinone Herbicides Imazamox,Imazapic, Imazaquin, and Imazamethabenz-methyl in Aqueous Solution. | J Agric Food Chem | 2015 Dec 23 | 26616105 |
| Photolysis pathway of imazapic in aqueous solution: ultrahigh resolution massspectrometry analysis of intermediates. | J Agric Food Chem | 2007 Nov 28 | 17960882 |
| Imidazolinone-tolerant crops: history, current status and future. | Pest Manag Sci | 2005 Mar | 15627242 |
| Haptens and monoclonal antibodies for immunoassay of imidazolinone herbicides. | J Agric Food Chem | 2002 Jun 5 | 12033799 |
Targets
- General Function:
- Type iii transforming growth factor beta receptor binding
- Specific Function:
- Multifunctional protein that controls proliferation, differentiation and other functions in many cell types. Many cells synthesize TGFB1 and have specific receptors for it. It positively and negatively regulates many other growth factors. It plays an important role in bone remodeling as it is a potent stimulator of osteoblastic bone formation, causing chemotaxis, proliferation and differentiation in committed osteoblasts. Can promote either T-helper 17 cells (Th17) or regulatory T-cells (Treg) lineage differentiation in a concentration-dependent manner. At high concentrations, leads to FOXP3-mediated suppression of RORC and down-regulation of IL-17 expression, favoring Treg cell development. At low concentrations in concert with IL-6 and IL-21, leads to expression of the IL-17 and IL-23 receptors, favoring differentiation to Th17 cells.
- Gene Name:
- TGFB1
- Uniprot ID:
- P01137
- Molecular Weight:
- 44340.685 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 ]