4-(2,2-difluorobenzo[d][1,3]dioxol-4-yl)-4H-pyrrole-3-carbonitrile

ID: ALA485833

Chembl Id: CHEMBL485833

Cas Number: 131341-86-1

PubChem CID: 86398

Product Number: F114615

Max Phase: Preclinical

Molecular Formula: C12H6F2N2O2

Molecular Weight: 248.19

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Fludioxonil | Fludioxonil|131341-86-1|4-(2,2-Difluorobenzo[d][1,3]dioxol-4-yl)-1H-pyrrole-3-carbonitrile|4-(2,2-Difluoro-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile|Scholar|1H-Pyrrole-3-carbonitrile, 4-(2,2-difluoro-1,3-benzodioxol-4-yl)-|Fludioxonil [ISO]|C12H6F2N2O2|ENS9J0YM16|DTXSID2032398|CHEBI:81763|Fludioxonil 10 microg/mL in Acetone|Fludioxonil 10 microg/mL in Acetonitrile|Saphire|Savior|Geoxe|Fludioxonil 100 microg/mL in Acetonitrile|Maxim|UNII-ENS9J0YM16|CGA 173506|Fludioxinil|MEDALShow More⌵

Canonical SMILES:  N#Cc1c[nH]cc1-c1cccc2c1OC(F)(F)O2

Standard InChI:  InChI=1S/C12H6F2N2O2/c13-12(14)17-10-3-1-2-8(11(10)18-12)9-6-16-5-7(9)4-15/h1-3,5-6,16H

Standard InChI Key:  MUJOIMFVNIBMKC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA485833

   FLUDIOXONIL

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

Calculated Properties

Molecular Weight: 248.19

Molecular Weight (Monoisotopic): 248.0397

AlogP: 2.87

#Rotatable Bonds: 1

Polar Surface Area: 58.04

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.57

CX LogD: 3.57

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.84

Np Likeness Score: -0.53

References

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2. Vetcher L, Menzella HG, Kudo T, Motoyama T, Katz L..  (2007)  The antifungal polyketide ambruticin targets the HOG pathway.,  51  (10): [PMID:17698623] [10.1128/aac.00369-07]

3. PubChem BioAssay data set, 

4. Dang QL, Kim WK, Nguyen CM, Choi YH, Choi GJ, Jang KS, Park MS, Lim CH, Luu NH, Kim JC..  (2011)  Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens.,  59  (20): [PMID:21910504] [10.1021/jf203017f]

5. Lee YM, Moon JS, Yun BS, Park KD, Choi GJ, Kim JC, Lee SH, Kim SU..  (2009)  Antifungal activity of CHE-23C, a dimeric sesquiterpene from Chloranthus henryi.,  57  (13): [PMID:19566082] [10.1021/jf900674y]

6. 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]

7. Hamada MS, Yin Y, Ma Z..  (2011)  Sensitivity to iprodione, difenoconazole and fludioxonil of Rhizoctonia cerealis isolates collected from wheat in China,  30  (8): [10.1016/j.cropro.2011.04.004]

8. Malandrakis AA, Markoglou AN, Ziogas BN..  (2012)  PCR-RFLP detection of the E198A mutation conferring resistance to benzimidazoles in field isolates of Monilinia laxa from Greece,  39  [10.1016/j.cropro.2012.04.001]

9. Petit AN, Fontaine F, Clément C, Vaillant-Gaveau N..  (2008)  Photosynthesis limitations of grapevine after treatment with the fungicide fludioxonil.,  56  (15): [PMID:18598040] [10.1021/jf800919u]

10. Kagabu S, Shimizu M, Mori M, Kurahashi Y, Yamaguchi I.  (2009)  N-Thiophenylethyl-2,2-dichloro-1-cyclopropanecarboxamides: modification of the amide part of carpropamid and examination of fungicidal activity,  34  (3): [10.1584/jpestics.G09-12]

11. Takagaki M, Kataoka S, Kida K, Miura I, Fukumoto S, Tamai R.  (2010)  Disease-controlling effect of a novel fungicide pyribencarb against Botrytis cinerea,  35  (1): [10.1584/jpestics.G09-24]

12. 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]

13. Veloukas T, Karaoglanidis GS..  (2012)  Biological activity of the succinate dehydrogenase inhibitor fluopyram against Botrytis cinerea and fungal baseline sensitivity.,  68  (6): [PMID:22262495] [10.1002/ps.3241]

14. PubChem BioAssay data set, 

15. Johnson BM, Shu YZ, Zhuo X, Meanwell NA..  (2020)  Metabolic and Pharmaceutical Aspects of Fluorinated Compounds.,  63  (12): [PMID:32182061] [10.1021/acs.jmedchem.9b01877]

16. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• IMI-CARE SARS-CoV-2 Data