Ethyl 3,5-Dimethyl-4-((6-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrrole-2-carboxylate

ID: ALA4636879

PubChem CID: 156011562

Max Phase: Preclinical

Molecular Formula: C16H17F3N2O2

Molecular Weight: 326.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1[nH]c(C)c(Cc2ccc(C(F)(F)F)nc2)c1C

Standard InChI:  InChI=1S/C16H17F3N2O2/c1-4-23-15(22)14-9(2)12(10(3)21-14)7-11-5-6-13(20-8-11)16(17,18)19/h5-6,8,21H,4,7H2,1-3H3

Standard InChI Key:  RMFOCEZBWXODRV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   19.6072  -21.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3926  -21.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0802  -22.2769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7172  -21.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4274  -20.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6244  -22.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5098  -21.9799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7223  -22.7742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0941  -21.4002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8867  -21.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4710  -21.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8793  -20.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0914  -20.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2797  -20.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7718  -19.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9607  -20.0029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6599  -20.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1804  -21.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9896  -21.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8524  -20.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3357  -20.2586    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.5534  -21.6613    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.0231  -20.8879    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  2  6  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  5 12  1  0
  1 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4636879

   ---

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: 326.32

Molecular Weight (Monoisotopic): 326.1242

AlogP: 3.81

#Rotatable Bonds: 4

Polar Surface Area: 54.98

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.72

CX LogP: 4.18

CX LogD: 4.18

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.87

Np Likeness Score: -1.15

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