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

ID: ALA385652

PubChem CID: 44417062

Max Phase: Preclinical

Molecular Formula: C21H17ClN2O2

Molecular Weight: 364.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1c(C#N)c(-c2ccc(-c3ccc(Cl)cc3)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)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:  OQBPVPMUCZTJAB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -0.6176   -3.3566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0665   -2.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1621   -2.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9855   -2.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2710   -2.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6451   -4.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0644   -3.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6551   -2.5020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633   -3.8735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3416   -1.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8489   -0.7963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4497   -1.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0858   -0.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5494    0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734   -0.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7316   -0.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2698   -1.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8385    0.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4734    1.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9379    2.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7618    2.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1191    1.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6564    0.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8387   -3.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828   -3.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2245    2.7002    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
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA385652

   3-(4''-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: -0.81

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