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

ID: ALA384847

PubChem CID: 11291212

Max Phase: Preclinical

Molecular Formula: C22H17N3O2

Molecular Weight: 355.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: LY-2059346 | CHEMBL384847|SCHEMBL4378272|FTBDCNMILMQXBY-UHFFFAOYSA-N|BDBM50191952|LY-2059346|4-cyano-3-(2''-cyano-biphenyl-4-yl)-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid|4-cyano-3-(2'-cyano-biphenyl-4-yl)-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid|4-cyano-3-[4-(2-cyanophenyl)phenyl]-5-ethyl-1-methylpyrrole-2-carboxylic acid

Canonical SMILES:  CCc1c(C#N)c(-c2ccc(-c3ccccc3C#N)cc2)c(C(=O)O)n1C

Standard InChI:  InChI=1S/C22H17N3O2/c1-3-19-18(13-24)20(21(22(26)27)25(19)2)15-10-8-14(9-11-15)17-7-5-4-6-16(17)12-23/h4-11H,3H2,1-2H3,(H,26,27)

Standard InChI Key:  FTBDCNMILMQXBY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   14.1804  -11.1970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8644  -10.7328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6359   -9.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8126   -9.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5271  -10.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1530  -12.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7337  -10.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1430  -10.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5348  -11.7138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1396   -9.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6469   -8.6368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3483   -9.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7123   -8.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2488   -7.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4248   -7.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0665   -8.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5284   -9.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9597   -7.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3247   -6.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8603   -5.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0365   -5.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6792   -6.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1419   -7.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6366  -11.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7807  -11.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1438   -6.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9630   -6.3266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  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
 12 13  2  0
 26 27  3  0
 19 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA384847

   4-Cyano-3-[4-(2-cyanophenyl)phenyl]-5-ethyl-1-methylpyrrole-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: 355.40

Molecular Weight (Monoisotopic): 355.1321

AlogP: 4.36

#Rotatable Bonds: 4

Polar Surface Area: 89.81

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.38

CX Basic pKa: ┄

CX LogP: 4.58

CX LogD: 1.17

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: -0.79

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