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

ID: ALA215575

Cas Number: 851196-32-2

PubChem CID: 44417040

Max Phase: Preclinical

Molecular Formula: C21H17FN2O2

Molecular Weight: 348.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1c(C#N)c(-c2ccc(-c3ccccc3F)cc2)c(C(=O)O)n1C

Standard InChI:  InChI=1S/C21H17FN2O2/c1-3-18-16(12-23)19(20(21(25)26)24(18)2)14-10-8-13(9-11-14)15-6-4-5-7-17(15)22/h4-11H,3H2,1-2H3,(H,25,26)

Standard InChI Key:  ONOQSBGHIPAOLO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.1369  -26.0790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8209  -25.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5924  -24.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7691  -24.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4836  -25.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1095  -26.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6902  -25.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0996  -25.2247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4914  -26.5958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0961  -24.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6033  -23.5191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3048  -24.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6688  -23.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2053  -22.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3814  -22.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0231  -23.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4850  -24.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9163  -22.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2814  -21.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8169  -20.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9931  -20.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6358  -21.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985  -22.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5931  -25.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7371  -26.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1005  -21.2677    0.0000 F   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
 19 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA215575

   4-cyano-5-ethyl-3-(2'-fluoro-[1,1'-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: 348.38

Molecular Weight (Monoisotopic): 348.1274

AlogP: 4.63

#Rotatable Bonds: 4

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: 3.38

CX Basic pKa: ┄

CX LogP: 4.87

CX LogD: 1.46

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.75

Np Likeness Score: -0.92

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