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

ID: ALA262219

PubChem CID: 44416888

Max Phase: Preclinical

Molecular Formula: C22H20N2O2S

Molecular Weight: 376.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Sc1c(C#N)c(-c2ccc(-c3ccccc3)cc2)c(C(=O)O)n1C

Standard InChI:  InChI=1S/C22H20N2O2S/c1-14(2)27-21-18(13-23)19(20(22(25)26)24(21)3)17-11-9-16(10-12-17)15-7-5-4-6-8-15/h4-12,14H,1-3H3,(H,25,26)

Standard InChI Key:  IKJDCTSVMTYEMX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.1949   -4.9391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -4.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442   -3.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8204   -3.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5377   -4.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1654   -5.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458   -4.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1513   -4.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5482   -5.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1535   -3.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6549   -2.3759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3589   -2.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187   -2.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2620   -1.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4376   -1.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0758   -2.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5383   -3.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281   -0.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3328   -0.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1288    0.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9531    0.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3140   -0.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8467   -0.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6490   -4.7548    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2789   -4.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0553   -4.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324   -3.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  1  6  1  0
 12 13  2  0
 24 25  1  0
 13 14  1  0
 25 26  1  0
  5  7  1  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA262219

   3-biphenyl-4-yl-4-cyano-5-isopropylsulfanyl-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: 376.48

Molecular Weight (Monoisotopic): 376.1245

AlogP: 5.43

#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: 3.35

CX Basic pKa: ┄

CX LogP: 5.29

CX LogD: 1.87

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: -0.70

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