Kresoxim-methyl

ID: ALA203191

Cas Number: 143390-89-0

PubChem CID: 6112114

Product Number: K109897, Order Now?

Max Phase: Preclinical

Molecular Formula: C18H19NO4

Molecular Weight: 313.35

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Kresoxim-Methyl | Kresoxim-Methyl|143390-89-0|Bas 490 F|Bas 490F|Kresoxim-methyl [ISO]|HSDB 7020|CHEBI:2962|methyl (2E)-2-methoxyimino-2-[2-[(2-methylphenoxy)methyl]phenyl]acetate|0LXZ062TTB|DTXSID2032558|Methyl (E)-alpha-(methoxyimino)-2-((2-methylphenoxy)methyl)benzeneacetate|methyl 2-methoxyimino-2-[2-[(2-methylphenoxy)methyl]phenyl]acetate|Candit|Stroby|kresoxim methyl ester|UNII-0LXZ062TTB|kresoxim methyl|EINECS Annex I Index 607-310-00-0|MFCD00871777|BAS-490 F|BAS-490-02F|Kresoxim-methyl 1Show More⌵

Canonical SMILES:  CO/N=C(/C(=O)OC)c1ccccc1COc1ccccc1C

Standard InChI:  InChI=1S/C18H19NO4/c1-13-8-4-7-11-16(13)23-12-14-9-5-6-10-15(14)17(19-22-3)18(20)21-2/h4-11H,12H2,1-3H3/b19-17+

Standard InChI Key:  ZOTBXTZVPHCKPN-HTXNQAPBSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -2.1807  -14.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4646  -14.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1807  -13.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8926  -14.6243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4646  -15.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7527  -15.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7527  -16.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4646  -17.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1807  -16.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1807  -15.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0366  -15.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6794  -15.8639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913  -15.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074  -15.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8235  -15.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8235  -14.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074  -14.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913  -14.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074  -16.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7527  -14.2139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0366  -14.6243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6794  -14.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8926  -15.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 12 13  1  0
 14 19  1  0
 11 12  1  0
  6 11  1  0
  2  5  1  0
 20 21  1  0
 21 22  1  0
  2 20  2  0
  4 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA203191

   KRESOXIM-METHYL

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 313.35

Molecular Weight (Monoisotopic): 313.1314

AlogP: 3.10

#Rotatable Bonds: 6

Polar Surface Area: 57.12

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.34

CX LogD: 4.34

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.47

Np Likeness Score: -0.36

References

1. Li Y, Liu J, Zhang H, Yang X, Liu Z..  (2006)  Stereoselective synthesis and fungicidal activities of (E)-alpha-(methoxyimino)-benzeneacetate derivatives containing 1,3,4-oxadiazole ring.,  16  (8): [PMID:16455246] [10.1016/j.bmcl.2006.01.026]

2. Engelmeier D, Hadacek F, Hofer O, Lutz-Kutschera G, Nagl M, Wurz G, Greger H..  (2004)  Antifungal 3-butylisocoumarins from Asteraceae-Anthemideae.,  67  (1): [PMID:14738379] [10.1021/np0301339]

3. PubChem BioAssay data set, 

4. Tu S, Xu LH, Ye LY, Wang X, Sha Y, Xiao ZY..  (2008)  Synthesis and fungicidal activities of novel indene-substituted oxime ether strobilurins.,  56  (13): [PMID:18547049] [10.1021/jf800273t]

5. Li M, Liu CL, Yang JC, Zhang JB, Li ZN, Zhang H, Li ZM..  (2010)  Synthesis and biological activity of new (E)-alpha-(Methoxyimino)benzeneacetate derivatives containing a substituted pyrazole ring.,  58  (5): [PMID:19961182] [10.1021/jf9026348]

6. Huang W, Zhao PL, Liu CL, Chen Q, Liu ZM, Yang GF..  (2007)  Design, synthesis, and fungicidal activities of new strobilurin derivatives.,  55  (8): [PMID:17371044] [10.1021/jf0632987]

7. Zhao PL, Wang F, Zhang MZ, Liu ZM, Huang W, Yang GF..  (2008)  Synthesis, fungicidal, and insecticidal activities of beta-Methoxyacrylate-containing N-acetyl pyrazoline derivatives.,  56  (22): [PMID:18973342] [10.1021/jf802343p]

8. Meyer MC, Bueno CJ, Souza NLd, Yorinori JT..  (2006)  Effect of doses of fungicides and plant resistance activators on the control of Rhizoctonia foliar blight of soybean, and on Rhizoctonia solani AG1-IA in vitro development,  25  (8): [10.1016/j.cropro.2005.11.008]

9. Nel B, Steinberg C, Labuschagne N, Viljoen A..  (2007)  Evaluation of fungicides and sterilants for potential application in the management of Fusarium wilt of banana,  26  (4): [10.1016/j.cropro.2006.06.008]

10. Zhao PL, Liu CL, Huang W, Wang YZ, Yang GF..  (2007)  Synthesis and fungicidal evaluation of novel chalcone-based strobilurin analogues.,  55  (14): [PMID:17579441] [10.1021/jf071064x]

11. Li Y, Zhang HQ, Liu J, Yang XP, Liu ZJ..  (2006)  Stereoselective synthesis and antifungal activities of (E)-alpha-(methoxyimino)benzeneacetate derivatives containing 1,3,5-substituted pyrazole ring.,  54  (10): [PMID:19127737] [10.1021/jf060074f]

12. Zhang CQ, Liu YH, Ma XY, Feng Z, Ma ZH..  (2009)  Characterization of sensitivity of Rhizoctonia solani, causing rice sheath blight, to mepronil and boscalid,  28  (5): [10.1016/j.cropro.2008.12.004]

13. Zhao PL, Wang L, Zhu XL, Huang X, Zhan CG, Wu JW, Yang GF..  (2010)  Subnanomolar inhibitor of cytochrome bc1 complex designed by optimizing interaction with conformationally flexible residues.,  132  (1): [PMID:19928849] [10.1021/ja905756c]

14. Haramoto M, Hamamura H, Sano S, Felsenstein FG, Otani H.  (2006)  Sensitivity monitoring of powdery mildew pathogens to cyflufenamid and the evaluation of resistance risk,  31  (4): [10.1584/jpestics.G06-13]

15. Li M, Liu CL, Li L, Yang H, Li ZN, Zhang H, Li ZM..  (2010)  Design, synthesis and biological activities of new strobilurin derivatives containing substituted pyrazoles.,  66  (1): [PMID:19760633] [10.1002/ps.1837]

16. ICHIBA T, MURASHI T, OHTSUKA T, MASUKO M.  (2002)  Fungicidal Activities of -Methoxyphenylacetic Acid Derivatives,  27  (2): [10.1584/jpestics.27.118]

17. ICHIBA T, INUTA T, HORITA Y, NIIKAWA M, MASUKO M.  (2002)  Controlling Efficacy of Strobilurin Derivatives against Wheat Powdery Mildew and Eyespot,  27  (2): [10.1584/jpestics.27.127]

18. Guan AY, Liu CL, Li M, Zhang H, Li ZN, Li ZM..  (2011)  Design, synthesis and structure-activity relationship of novel coumarin derivatives.,  67  (6): [PMID:21305686] [10.1002/ps.2103]

19. De Miccolis Angelini RM, Rotolo C, Masiello M, Pollastro S, Ishii H, Faretra F..  (2012)  Genetic analysis and molecular characterisation of laboratory and field mutants of Botryotinia fuckeliana (Botrytis cinerea) resistant to QoI fungicides.,  68  (9): [PMID:22488841] [10.1002/ps.3281]

20. PubChem BioAssay data set, 

21. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

22. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

23. Institute for Molecular Medicine Finland - High Throughput Biomedicine Unit.  (2023)  ECBD screening data for assay EOS300108,  [10.6019/EOS300108]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• SARS-CoV-2 Screening Data 2020-21
• EU-OPENSCREEN dataset