Ethyl 3,5-Dimethyl-4-(4-(trifluoromethyl)benzyl)-1H-pyrrole-2-carboxylate

ID: ALA4642145

PubChem CID: 146020611

Max Phase: Preclinical

Molecular Formula: C17H18F3NO2

Molecular Weight: 325.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1[nH]c(C)c(Cc2ccc(C(F)(F)F)cc2)c1C

Standard InChI:  InChI=1S/C17H18F3NO2/c1-4-23-16(22)15-10(2)14(11(3)21-15)9-12-5-7-13(8-6-12)17(18,19)20/h5-8,21H,4,9H2,1-3H3

Standard InChI Key:  PWRCYLHLZGCFQH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    6.0576  -12.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8429  -13.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5305  -14.1462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1675  -13.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8777  -12.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0747  -13.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9601  -13.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1726  -14.6436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5444  -13.2696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3370  -13.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9213  -12.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3296  -12.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417  -12.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7300  -12.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2221  -11.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4110  -11.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102  -12.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6307  -13.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4399  -13.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027  -12.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860  -12.1279    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0037  -13.5306    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4734  -12.7573    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:

   

   ALA4642145

   ---

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: 325.33

Molecular Weight (Monoisotopic): 325.1290

AlogP: 4.42

#Rotatable Bonds: 4

Polar Surface Area: 42.09

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.02

CX LogD: 5.02

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.85

Np Likeness Score: -1.03

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