2-{4-[5-(4-Fluoro-phenyl)-4-pyridin-4-yl-1H-pyrrol-2-yl]-piperidin-1-yl}-1-methyl-ethylamine

ID: ALA364448

PubChem CID: 44399677

Max Phase: Preclinical

Molecular Formula: C23H27FN4

Molecular Weight: 378.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(N)CN1CCC(c2cc(-c3ccncc3)c(-c3ccc(F)cc3)[nH]2)CC1

Standard InChI:  InChI=1S/C23H27FN4/c1-16(25)15-28-12-8-18(9-13-28)22-14-21(17-6-10-26-11-7-17)23(27-22)19-2-4-20(24)5-3-19/h2-7,10-11,14,16,18,27H,8-9,12-13,15,25H2,1H3

Standard InChI Key:  DTALPIMAXWLLKW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    0.0917   -3.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -3.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -2.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -2.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -3.2875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208   -3.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4958   -0.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375   -3.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -4.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0375   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0458   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7500   -4.8167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.4292   -4.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375   -0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625   -1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  1  0
  5  3  1  0
  6 17  1  0
  7  1  1  0
  8  4  1  0
  9  3  1  0
 10 25  1  0
 11  7  2  0
 12  7  1  0
 13  8  1  0
 14  8  1  0
 15  6  1  0
 16 13  1  0
 17 14  1  0
 18 19  1  0
 19 12  2  0
 20 11  1  0
 21 18  1  0
 22 23  1  0
 23 15  1  0
 24 26  1  0
 25 27  2  0
 26  9  2  0
 27  9  1  0
 28 23  1  0
  4  5  2  0
 20 18  2  0
 24 10  2  0
 16  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA364448

   2-{4-[5-(4-Fluoro-phenyl)-4-pyridin-4-yl-1H-pyrrol-2-yl]-piperidin-1-yl}-1-methyl-ethylamine

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: 378.50

Molecular Weight (Monoisotopic): 378.2220

AlogP: 4.41

#Rotatable Bonds: 5

Polar Surface Area: 57.94

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.72

CX LogP: 3.14

CX LogD: 0.76

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.69

Np Likeness Score: -0.78

References

1. Biftu T, Feng D, Ponpipom M, Girotra N, Liang GB, Qian X, Bugianesi R, Simeone J, Chang L, Gurnett A, Liberator P, Dulski P, Leavitt PS, Crumley T, Misura A, Murphy T, Rattray S, Samaras S, Tamas T, Mathew J, Brown C, Thompson D, Schmatz D, Fisher M, Wyvratt M..  (2005)  Synthesis and SAR of 2,3-diarylpyrrole inhibitors of parasite cGMP-dependent protein kinase as novel anticoccidial agents.,  15  (13): [PMID:15922595] [10.1016/j.bmcl.2005.04.060]

Source

Source(1):

• Scientific Literature