3-biphenyl-4-yl-5-bromo-4-cyano-1-methyl-1H-pyrrole-2-carboxylic acid

ID: ALA385704

PubChem CID: 44416905

Max Phase: Preclinical

Molecular Formula: C19H13BrN2O2

Molecular Weight: 381.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(Br)c(C#N)c(-c2ccc(-c3ccccc3)cc2)c1C(=O)O

Standard InChI:  InChI=1S/C19H13BrN2O2/c1-22-17(19(23)24)16(15(11-21)18(22)20)14-9-7-13(8-10-14)12-5-3-2-4-6-12/h2-10H,1H3,(H,23,24)

Standard InChI Key:  GBUJJYBSRJRTJJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   13.0673  -10.4699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7506  -10.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5223   -9.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6997   -9.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4145   -9.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0399  -11.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6220  -10.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0319   -9.6162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4233  -10.9862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0255   -8.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5321   -7.9123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2360   -8.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5995   -7.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1365   -7.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3133   -7.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9555   -7.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4168   -8.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8487   -6.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2134   -5.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7495   -5.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9264   -5.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5695   -5.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0317   -6.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5259  -10.2891    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  4 12  1  0
  1  6  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA385704

   3-biphenyl-4-yl-5-bromo-4-cyano-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: 381.23

Molecular Weight (Monoisotopic): 380.0160

AlogP: 4.69

#Rotatable Bonds: 3

Polar Surface Area: 66.02

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.33

CX Basic pKa: ┄

CX LogP: 4.47

CX LogD: 1.05

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -0.55

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