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

ID: ALA214599

PubChem CID: 44417019

Max Phase: Preclinical

Molecular Formula: C21H17FN2O2

Molecular Weight: 348.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1c(C#N)c(-c2ccc(-c3ccc(F)cc3)cc2)c(C(=O)O)n1C

Standard InChI:  InChI=1S/C21H17FN2O2/c1-3-18-17(12-23)19(20(21(25)26)24(18)2)15-6-4-13(5-7-15)14-8-10-16(22)11-9-14/h4-11H,3H2,1-2H3,(H,25,26)

Standard InChI Key:  QZYOGWGIQJFWQU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   14.1736  -19.3991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8577  -18.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6291  -18.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8057  -18.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5202  -18.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1462  -20.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7268  -19.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1361  -18.5446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5279  -19.9159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1329  -17.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6401  -16.8388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3415  -17.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7054  -16.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2419  -16.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4178  -16.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0596  -16.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5214  -17.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9527  -15.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3178  -14.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8534  -13.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0294  -14.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6722  -14.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1348  -15.4488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6299  -19.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7740  -20.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5667  -13.3423    0.0000 F   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
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA214599

   4-cyano-5-ethyl-3-(4''-fluoro-biphenyl-4-yl)-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: 348.38

Molecular Weight (Monoisotopic): 348.1274

AlogP: 4.63

#Rotatable Bonds: 4

Polar Surface Area: 66.02

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.38

CX Basic pKa: ┄

CX LogP: 4.87

CX LogD: 1.46

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.75

Np Likeness Score: -0.90

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