ID: ALA522782

Max Phase: Preclinical

Molecular Formula: C15H16Cl3N3O2

Molecular Weight: 376.67

Molecule Type: Small molecule

Representations

Synonyms (1): Prochloraz
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCCN(CCOc1c(Cl)cc(Cl)cc1Cl)C(=O)n1ccnc1

Standard InChI:  InChI=1S/C15H16Cl3N3O2/c1-2-4-20(15(22)21-5-3-19-10-21)6-7-23-14-12(17)8-11(16)9-13(14)18/h3,5,8-10H,2,4,6-7H2,1H3

Standard InChI Key:  TVLSRXXIMLFWEO-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 376.67

Molecular Weight (Monoisotopic): 375.0308

AlogP: 4.60

#Rotatable Bonds: 6

Polar Surface Area: 47.36

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 2.55

CX LogP: 3.62

CX LogD: 3.62

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.74

Np Likeness Score: -1.42

References

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2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

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5. 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]

6. Cohen R, Omari N, Porat A, Edelstein M..  (2012)  Management of Macrophomina wilt in melons using grafting or fungicide soil application: Pathological, horticultural and economical aspects,  35  [10.1016/j.cropro.2011.12.015]

7. KAI H, ICHIBA T, TOMIDA M, MASUKO M.  (1999)  Synthesis and Fungicidal Activities of 3-(-Alkoxyiminobenzyl)isoxazole Derivatives,  24  (2): [10.1584/jpestics.24.149]

8. Niewiadomy A, Matysiak J, Fekner Z, Czeczko R.  (2006)  Synthesis, antifungal activity and SAR of N-substituted and N,N-disubstituted 2,4-dihydroxythiobenzamides,  31  (1): [10.1584/jpestics.31.14]

9. 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]

10. Malandrakis A, Koukiasas N, Veloukas T, Karaoglanidis G, Markoglou A..  (2013)  Baseline sensitivity of Monilinia laxa from Greece to fenhexamid and analysis of fenhexamid-resistant mutants,  46  [10.1016/j.cropro.2012.12.009]

11. Amponsah NT, Jones E, Ridgway HJ, Jaspers MV..  (2012)  Evaluation of fungicides for the management of Botryosphaeria dieback diseases of grapevines.,  68  (5): [PMID:22290833] [10.1002/ps.2309]

12. Cools HJ, Bayon C, Atkins S, Lucas JA, Fraaije BA..  (2012)  Overexpression of the sterol 14α-demethylase gene (MgCYP51) in Mycosphaerella graminicola isolates confers a novel azole fungicide sensitivity phenotype.,  68  (7): [PMID:22411894] [10.1002/ps.3263]

13. Leroux P, Gredt M, Remuson F, Micoud A, Walker AS..  (2013)  Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.,  69  (1): [PMID:23073993] [10.1002/ps.3408]

14. PubChem BioAssay data set, 

15. PubChem BioAssay data set, 

16. Zhou XM, Zheng CJ, Gan LS, Chen GY, Zhang XP, Song XP, Li GN, Sun CG..  (2016)  Bioactive Phenanthrene and Bibenzyl Derivatives from the Stems of Dendrobium nobile.,  79  (7): [PMID:27310249] [10.1021/acs.jnatprod.6b00252]

17. Lin L, Dai Y, Xia Y..  (2022)  An overview of aryl hydrocarbon receptor ligands in the Last two decades (2002-2022): A medicinal chemistry perspective.,  244  [PMID:36274276] [10.1016/j.ejmech.2022.114845]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays