4-[2-(4-Fluorophenyl)-4-(1,2,2,6,6-pentamethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrol-3-yl]pyridine

ID: ALA1091637

PubChem CID: 9952305

Max Phase: Preclinical

Molecular Formula: C25H28FN3

Molecular Weight: 389.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(C)(C)C=C(c2c[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1(C)C

Standard InChI:  InChI=1S/C25H28FN3/c1-24(2)14-19(15-25(3,4)29(24)5)21-16-28-23(18-6-8-20(26)9-7-18)22(21)17-10-12-27-13-11-17/h6-14,16,28H,15H2,1-5H3

Standard InChI Key:  SDJKTRLZFNOBTM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -2.4223  -16.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7409  -17.1168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0896  -16.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3686  -15.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924  -15.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6134  -15.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066  -14.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6266  -13.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4532  -13.7340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8581  -14.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4357  -15.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1334  -17.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8516  -16.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5635  -17.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5585  -17.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8356  -18.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1266  -17.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9498  -15.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230  -15.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2925  -14.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1141  -13.6999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9408  -13.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610  -14.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2704  -18.3225    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3043  -12.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6599  -13.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5338  -12.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7007  -15.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886  -14.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 14 15  2  0
  7  8  1  0
 15 16  1  0
  3  4  2  0
 16 17  2  0
 17 12  1  0
  1 12  1  0
 18 19  2  0
  8  9  2  0
  4  5  1  0
  9 10  1  0
  5  1  2  0
 10 11  2  0
 11  6  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  4 18  1  0
  5  6  1  0
 15 24  1  0
  1  2  1  0
 21 25  1  0
 22 26  1  0
 12 13  2  0
 22 27  1  0
  6  7  2  0
 20 28  1  0
 13 14  1  0
 20 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091637

   4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1H-pyrrol-3-yl]-1,2,2,6,6-pentamethyl-3H-pyridine

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: 389.52

Molecular Weight (Monoisotopic): 389.2267

AlogP: 6.16

#Rotatable Bonds: 3

Polar Surface Area: 31.92

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.84

CX LogP: 4.96

CX LogD: 2.56

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -0.26

References

1. Nakao A, Ohkawa N, Nagasaki T, Kagari T, Doi H, Shimozato T, Ushiyama S, Aoki K..  (2010)  Tetrahydropyridine derivatives with inhibitory activity on the production of proinflammatory cytokines: part 2.,  20  (8): [PMID:20346666] [10.1016/j.bmcl.2010.03.022]

2. Nakao A, Ohkawa N, Nagasaki T, Kagari T, Doi H, Shimozato T, Ushiyama S, Aoki K..  (2010)  Tetrahydropyridine derivatives with inhibitory activity on the production of proinflammatory cytokines: part 3.,  20  (16): [PMID:20637613] [10.1016/j.bmcl.2010.06.122]

Source

Source(1):

• Scientific Literature