ID: ALA203191

Max Phase: Preclinical

Molecular Formula: C18H19NO4

Molecular Weight: 313.35

Molecule Type: Small molecule

Representations

Synonyms (1): Kresoxim-Methyl
Synonyms from Alternative Forms(1):

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

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

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: 0

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

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

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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]

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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]

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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]

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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]

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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]

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Source

Source(4):

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