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

ID: ALA217074

PubChem CID: 44417063

Max Phase: Preclinical

Molecular Formula: C21H17ClN2O2

Molecular Weight: 364.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1c(C#N)c(-c2ccc(-c3cccc(Cl)c3)cc2)c(C(=O)O)n1C

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

Standard InChI Key:  JPAOOYFLLXHRNZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    6.5495   -3.5309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2335   -3.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0050   -2.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1815   -2.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8960   -3.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5220   -4.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1026   -3.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5119   -2.6764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9037   -4.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5087   -1.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0159   -0.9706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7173   -1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0812   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6177   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7937   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4354   -0.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8972   -1.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3285    0.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6936    1.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292    1.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4052    1.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0480    1.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5107    0.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0058   -3.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1498   -4.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5870    2.6460    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
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA217074

   3-(3''-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: -0.95

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