Ethyl 4-(4-Methoxybenzyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate

ID: ALA4649039

PubChem CID: 156020772

Max Phase: Preclinical

Molecular Formula: C17H21NO3

Molecular Weight: 287.36

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H21NO3/c1-5-21-17(19)16-11(2)15(12(3)18-16)10-13-6-8-14(20-4)9-7-13/h6-9,18H,5,10H2,1-4H3

Standard InChI Key:  VZQQHRJTOPINCI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   25.9673  -12.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7527  -13.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4402  -13.9564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0814  -13.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7875  -12.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9845  -13.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8740  -13.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0824  -14.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4542  -13.0797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2468  -13.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8310  -12.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2394  -11.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4556  -12.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6438  -12.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1318  -11.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3207  -11.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0241  -12.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5405  -13.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3497  -12.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2125  -12.5745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6958  -11.9381    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA4649039

   ---

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: 287.36

Molecular Weight (Monoisotopic): 287.1521

AlogP: 3.41

#Rotatable Bonds: 5

Polar Surface Area: 51.32

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.98

CX LogD: 3.98

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.86

Np Likeness Score: -0.70

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