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

ID: ALA214804

PubChem CID: 44416892

Max Phase: Preclinical

Molecular Formula: C22H17N3O2

Molecular Weight: 355.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1c(C#N)c(-c2ccc(-c3cccc(C#N)c3)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)16-9-7-15(8-10-16)17-6-4-5-14(11-17)12-23/h4-11H,3H2,1-2H3,(H,26,27)

Standard InChI Key:  RXPDWHUHHQMZGM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.2851  -11.5076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9691  -11.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7406  -10.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9172  -10.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6316  -10.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2575  -12.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8382  -11.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2476  -10.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6394  -12.0245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2442   -9.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7515   -8.9474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4529   -9.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8168   -8.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3532   -8.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5293   -8.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1710   -8.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6329   -9.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0641   -7.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292   -6.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9647   -6.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1408   -6.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7835   -6.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2463   -7.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7413  -11.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8854  -12.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3225   -5.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6804   -4.5916    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
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA214804

   4-cyano-3-(3''-cyano-biphenyl-4-yl)-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: 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: -0.88

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