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

ID: ALA215090

PubChem CID: 11773296

Max Phase: Preclinical

Molecular Formula: C22H20N2O2S

Molecular Weight: 376.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1c(C#N)c(-c2ccc(-c3ccccc3SC)cc2)c(C(=O)O)n1C

Standard InChI:  InChI=1S/C22H20N2O2S/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:  BFVMMSQKTYYTMS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.4078  -18.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1793  -17.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3559  -17.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0703  -18.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6964  -19.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2770  -18.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6863  -17.8899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0781  -19.2613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6830  -16.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1902  -16.1841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8916  -16.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2555  -16.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7921  -15.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9681  -15.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097  -16.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0716  -16.8383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028  -14.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8679  -13.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4035  -13.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5796  -13.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223  -14.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850  -14.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1801  -18.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3241  -19.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6873  -13.9325    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474  -13.1944    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:

   

   ALA215090

   4-cyano-5-ethyl-1-methyl-3-(2''-methylsulfanyl-biphenyl-4-yl)-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: 376.48

Molecular Weight (Monoisotopic): 376.1245

AlogP: 5.21

#Rotatable Bonds: 5

Polar Surface Area: 66.02

Molecular Species: ACID

HBA: 4

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: 5.36

CX LogD: 1.95

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: -0.76

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