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

ID: ALA215013

PubChem CID: 44416834

Max Phase: Preclinical

Molecular Formula: C22H20N2O3

Molecular Weight: 360.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1c(C#N)c(-c2ccc(-c3ccccc3OC)cc2)c(C(=O)O)n1C

Standard InChI:  InChI=1S/C22H20N2O3/c1-4-18-17(13-23)20(21(22(25)26)24(18)2)15-11-9-14(10-12-15)16-7-5-6-8-19(16)27-3/h5-12H,4H2,1-3H3,(H,25,26)

Standard InChI Key:  BIFLCTAYAWDBGO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.7436  -10.9962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4277  -10.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1991   -9.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3757   -9.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0902  -10.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7162  -11.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2968  -10.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7061  -10.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0979  -11.5131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7029   -9.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2101   -8.4360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9115   -9.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2754   -8.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8119   -7.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9878   -7.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6296   -8.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0914   -9.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5227   -6.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8878   -6.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4234   -5.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5994   -5.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2422   -6.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7048   -7.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1999  -10.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3439  -11.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7071   -6.1843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0672   -5.4462    0.0000 C   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
 19 26  1  0
 12 13  2  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA215013

   4-cyano-5-ethyl-3-(2''-methoxy-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: 360.41

Molecular Weight (Monoisotopic): 360.1474

AlogP: 4.50

#Rotatable Bonds: 5

Polar Surface Area: 75.25

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: 4.57

CX LogD: 1.16

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.73

Np Likeness Score: -0.59

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