Metrafenone
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Basic Info
| Common Name | Metrafenone(F05690) |
| 2D Structure | |
| FRCD ID | F05690 |
| CAS Number | 220899-03-6 |
| PubChem CID | 6451057 |
| Formula | C19H21BrO5 |
| IUPAC Name | (3-bromo-6-methoxy-2-methylphenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone |
| InChI Key | AMSPWOYQQAWRRM-UHFFFAOYSA-N |
| InChI | InChI=1S/C19H21BrO5/c1-10-9-14(23-4)18(24-5)19(25-6)15(10)17(21)16-11(2)12(20)7-8-13(16)22-3/h7-9H,1-6H3 |
| Canonical SMILES | CC1=CC(=C(C(=C1C(=O)C2=C(C=CC(=C2C)Br)OC)OC)OC)OC |
| Isomeric SMILES | CC1=CC(=C(C(=C1C(=O)C2=C(C=CC(=C2C)Br)OC)OC)OC)OC |
| Synonyms |
(3-bromo-6-methoxy-2-methylphenyl)(2,3,4-trimethoxy-6-methylphenyl)methanone
Metrafenone
220899-03-6
UNII-S04CWW41HM
S04CWW41HM
CHEBI:83345
BAS 560 02F
(3-bromo-6-methoxy-2-methylphenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone
Flexity
Vivando
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzophenones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzophenones |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Benzophenone - Diphenylmethane - Aryl-phenylketone - Anisole - Phenoxy compound - Benzoyl - Phenol ether - Aryl ketone - Methoxybenzene - Halobenzene - Bromobenzene - Toluene - Alkyl aryl ether - Aryl bromide - Aryl halide - Ketone - Ether - Organooxygen compound - Organobromide - Organohalogen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 409.276 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 6 |
| Complexity | 446 |
| Monoisotopic Mass | 408.057 |
| Exact Mass | 408.057 |
| XLogP | 4.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 25 |
| 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+ | 0.9353 |
| Human Intestinal Absorption | HIA+ | 0.9946 |
| Caco-2 Permeability | Caco2+ | 0.8290 |
| P-glycoprotein Substrate | Non-substrate | 0.6251 |
| P-glycoprotein Inhibitor | Inhibitor | 0.5356 |
| Non-inhibitor | 0.5554 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8573 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7724 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8231 |
| CYP450 2D6 Substrate | Non-substrate | 0.8314 |
| CYP450 3A4 Substrate | Substrate | 0.5122 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9009 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6780 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9036 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8499 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.6131 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8127 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9731 |
| Non-inhibitor | 0.9035 | |
| AMES Toxicity | Non AMES toxic | 0.9002 |
| Carcinogens | Non-carcinogens | 0.7887 |
| Fish Toxicity | High FHMT | 0.9828 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9982 |
| Honey Bee Toxicity | High HBT | 0.7871 |
| Biodegradation | Not ready biodegradable | 0.9595 |
| Acute Oral Toxicity | III | 0.6389 |
| Carcinogenicity (Three-class) | Non-required | 0.4164 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.7439 | LogS |
| Caco-2 Permeability | 1.5988 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6298 | LD50, mol/kg |
| Fish Toxicity | 0.4318 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.4899 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Citrus fruits | 0110000 | European Union | 0.01* | 05/06/2018 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 05/06/2018 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 05/06/2018 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 05/06/2018 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 05/06/2018 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.01* | 05/06/2018 | |
| Others (2) | 0110990 | European Union | 0.01* | 05/06/2018 | |
| Tree nuts | 0120000 | European Union | 0.01* | 05/06/2018 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.01* | 05/06/2018 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 05/06/2018 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 05/06/2018 | |
| Chestnuts | 0120040 | European Union | 0.01* | 05/06/2018 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 05/06/2018 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.01* | 05/06/2018 | |
| Macadamias | 0120070 | European Union | 0.01* | 05/06/2018 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.01* | 05/06/2018 | |
| Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ... | 0120090 | European Union | 0.01* | 05/06/2018 | |
| Walnuts | 0120110 | European Union | 0.01* | 05/06/2018 | |
| Others (2) | 0120990 | European Union | 0.01* | 05/06/2018 | |
| Pome fruits | 0130000 | European Union | 1 | 05/06/2018 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Biological Control of Botrytis cinerea: Interactions with Native Vineyard Yeasts from Washington State. | Phytopathology | 2018 Jun | 29334476 |
| Influence of the presence of ethanol on in vitro bioavailability of fungicideresidues. | Food Chem Toxicol | 2016 Jul | 27112541 |
| Metrafenone resistance in a population of Erysiphe necator in northern Italy. | Pest Manag Sci | 2016 Feb | 26079510 |
| Influence of new generation fungicides on Saccharomyces cerevisiae growth, grape must fermentation and aroma biosynthesis. | Food Chem | 2014 Mar 1 | 24176337 |
| Effect of two anti-fungal treatments (metrafenone and boscalid pluskresoxim-methyl) applied to vines on the color and phenol profile of differentred wines. | Molecules | 2014 Jun 16 | 24936710 |