(3,3-Difluoroazetidin-1-yl)(3-methyl-4-((6-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrrol-2-yl)methanone

ID: ALA4636553

PubChem CID: 156012404

Max Phase: Preclinical

Molecular Formula: C16H14F5N3O

Molecular Weight: 359.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(Cc2ccc(C(F)(F)F)nc2)c[nH]c1C(=O)N1CC(F)(F)C1

Standard InChI:  InChI=1S/C16H14F5N3O/c1-9-11(4-10-2-3-12(22-5-10)16(19,20)21)6-23-13(9)14(25)24-7-15(17,18)8-24/h2-3,5-6,23H,4,7-8H2,1H3

Standard InChI Key:  CTQHCGSVDQJGCJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   34.8008  -16.4594    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   34.5944  -17.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3818  -17.0338    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.3740  -17.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1676  -18.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8262  -18.9091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4385  -18.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1611  -17.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1981  -18.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4024  -19.3857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7959  -17.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9780  -17.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4076  -16.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5904  -16.8736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3457  -17.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9289  -18.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7439  -18.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5272  -17.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9517  -17.2595    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.2882  -18.6766    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.7114  -18.0855    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.6050  -16.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7798  -18.0546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5905  -18.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7829  -17.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  4  1  0
  7  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
  8 22  1  0
  9 23  1  0
 23 24  1  0
 24  2  1  0
  2 25  1  0
 25 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4636553

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 359.30

Molecular Weight (Monoisotopic): 359.1057

AlogP: 3.42

#Rotatable Bonds: 3

Polar Surface Area: 48.99

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.72

CX LogP: 3.45

CX LogD: 3.45

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.85

Np Likeness Score: -0.74

References

1. Kokkonda S, Deng X, White KL, El Mazouni F, White J, Shackleford DM, Katneni K, Chiu FCK, Barker H, McLaren J, Crighton E, Chen G, Angulo-Barturen I, Jimenez-Diaz MB, Ferrer S, Huertas-Valentin L, Martinez-Martinez MS, Lafuente-Monasterio MJ, Chittimalla R, Shahi SP, Wittlin S, Waterson D, Burrows JN, Matthews D, Tomchick D, Rathod PK, Palmer MJ, Charman SA, Phillips MA..  (2020)  Lead Optimization of a Pyrrole-Based Dihydroorotate Dehydrogenase Inhibitor Series for the Treatment of Malaria.,  63  (9): [PMID:32248693] [10.1021/acs.jmedchem.0c00311]

Source

Source(1):

• Scientific Literature