3-(2'-chloro-biphenyl-4-yl)-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid

ID: ALA384402

PubChem CID: 44417082

Max Phase: Preclinical

Molecular Formula: C21H17ClN2O2

Molecular Weight: 364.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1c(C#N)c(-c2ccc(-c3ccccc3Cl)cc2)c(C(=O)O)n1C

Standard InChI:  InChI=1S/C21H17ClN2O2/c1-3-18-16(12-23)19(20(21(25)26)24(18)2)14-10-8-13(9-11-14)15-6-4-5-7-17(15)22/h4-11H,3H2,1-2H3,(H,25,26)

Standard InChI Key:  PLYAKPPEYCWTLQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   13.8637   -3.1241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5478   -2.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3192   -1.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4958   -1.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2103   -2.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8362   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4169   -2.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8262   -2.2696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2180   -3.6410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8229   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3302   -0.5638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0316   -1.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3955   -0.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9319    0.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1079    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7497   -0.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2115   -1.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6428    0.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0079    1.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5434    2.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7195    2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3622    1.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8249    0.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3200   -2.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4641   -3.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8272    1.6877    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 13 14  1  0
  5  7  1  0
 14 15  2  0
  2  3  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 12  1  0
  3  4  1  0
 15 18  1  0
  7  9  2  0
 18 19  2  0
  4  5  2  0
 19 20  1  0
  5  1  1  0
 20 21  2  0
 10 11  3  0
 21 22  1  0
  3 10  1  0
 22 23  2  0
 23 18  1  0
  1  2  1  0
  2 24  1  0
  4 12  1  0
 24 25  1  0
  1  6  1  0
 19 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA384402

   3-(2''-chloro-biphenyl-4-yl)-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid

Molecule Features

Natural Product: No

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

Calculated Properties

Molecular Weight: 364.83

Molecular Weight (Monoisotopic): 364.0979

AlogP: 5.14

#Rotatable Bonds: 4

Polar Surface Area: 66.02

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.38

CX Basic pKa: ┄

CX LogP: 5.33

CX LogD: 1.92

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -0.84

References

1. Zarrinmayeh H, Tromiczak E, Zimmerman DM, Rankl N, Ho KH, Dominguez E, Castaño A, Escribano A, Fernandez C, Jimenez A, Hornback WJ, Nisenbaum ES..  (2006)  A novel class of positive allosteric modulators of AMPA receptors: design, synthesis, and structure-activity relationships of 3-biphenyl-4-yl-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid, LY2059346.,  16  (19): [PMID:16872827] [10.1016/j.bmcl.2006.07.012]

Source

Source(1):

• Scientific Literature