ID: ALA372700

Max Phase: Preclinical

Molecular Formula: C20H33NO

Molecular Weight: 303.49

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  CC(Cc1ccc(C(C)(C)C)cc1)CN1C[C@@H](C)O[C@@H](C)C1

Standard InChI:  InChI=1S/C20H33NO/c1-15(12-21-13-16(2)22-17(3)14-21)11-18-7-9-19(10-8-18)20(4,5)6/h7-10,15-17H,11-14H2,1-6H3/t15?,16-,17+

Standard InChI Key:  RYAUSSKQMZRMAI-ALOPSCKCSA-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: 303.49

Molecular Weight (Monoisotopic): 303.2562

AlogP: 4.27

#Rotatable Bonds: 4

Polar Surface Area: 12.47

Molecular Species: NEUTRAL

HBA: 2

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.49

CX LogP: 5.17

CX LogD: 4.05

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.82

Np Likeness Score: -0.84

References

1. Laggner C, Schieferer C, Fiechtner B, Poles G, Hoffmann RD, Glossmann H, Langer T, Moebius FF..  (2005)  Discovery of high-affinity ligands of sigma1 receptor, ERG2, and emopamil binding protein by pharmacophore modeling and virtual screening.,  48  (15): [PMID:16033255] [10.1021/jm049073+]

2. Hunt JC, Briggs E, Clarke ED, Whittingham WG..  (2007)  Synthesis and SAR studies of novel antifungal 1,2,3-triazines.,  17  (18): [PMID:17656087] [10.1016/j.bmcl.2007.06.076]

3. Meyer V, Damveld RA, Arentshorst M, Stahl U, van den Hondel CA, Ram AF..  (2007)  Survival in the presence of antifungals: genome-wide expression profiling of Aspergillus niger in response to sublethal concentrations of caspofungin and fenpropimorph.,  282  (45): [PMID:17804411] [10.1074/jbc.m705856200]

4. Hajipour AR, Fontanilla D, Chu UB, Arbabian M, Ruoho AE..  (2010)  Synthesis and characterization of N,N-dialkyl and N-alkyl-N-aralkyl fenpropimorph-derived compounds as high affinity ligands for sigma receptors.,  18  (12): [PMID:20493718] [10.1016/j.bmc.2010.04.078]

5. Laurini E, Col VD, Mamolo MG, Zampieri D, Posocco P, Fermeglia M, Vio L, Pricl S..  (2011)  Homology Model and Docking-Based Virtual Screening for Ligands of the σ1 Receptor.,  2  (11): [PMID:24900272] [10.1021/ml2001505]

6. Taton M, Benveniste P, Rahier A..  (1989)  Microsomal delta 8,14-sterol delta 14-reductase in higher plants. Characterization and inhibition by analogues of a presumptive carbocationic intermediate of the reduction reaction.,  185  (3): [PMID:2591378] [10.1111/j.1432-1033.1989.tb15156.x]

7. Berbegal M, Armengol J, García-Jiménez J..  (2011)  Evaluation of fungicides to control circular leaf spot of persimmon caused by Mycosphaerella nawae,  30  (11): [10.1016/j.cropro.2011.05.017]

8. 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]

9. 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]

10. Settimo L, Bellman K, Knegtel RM..  (2013)  Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.,  [PMID:24249037] [10.1007/s11095-013-1232-z]

11. Brune S, Pricl S, Wünsch B..  (2013)  Structure of the σ1 receptor and its ligand binding site.,  56  (24): [PMID:23964901] [10.1021/jm400660u]

12. PubChem BioAssay data set, 

13. Jachak GR, Ramesh R, Sant DG, Jorwekar SU, Jadhav MR, Tupe SG, Deshpande MV, Reddy DS..  (2015)  Silicon Incorporated Morpholine Antifungals: Design, Synthesis, and Biological Evaluation.,  6  (11): [PMID:26617963] [10.1021/acsmedchemlett.5b00245]

14. Sguazzini E, Schmidt HR, Iyer KA, Kruse AC, Dukat M..  (2017)  Reevaluation of fenpropimorph as a σ receptor ligand: Structure-affinity relationship studies at human σ1 receptors.,  27  (13): [PMID:28495085] [10.1016/j.bmcl.2017.04.088]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays