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

ID: ALA1093562

PubChem CID: 9880738

Max Phase: Preclinical

Molecular Formula: C21H20FN3

Molecular Weight: 333.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC=C(c2c[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1

Standard InChI:  InChI=1S/C21H20FN3/c1-25-12-8-15(9-13-25)19-14-24-21(17-2-4-18(22)5-3-17)20(19)16-6-10-23-11-7-16/h2-8,10-11,14,24H,9,12-13H2,1H3

Standard InChI Key:  CQWRMGCHJURACZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    4.7580   -0.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4400   -0.5637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0916   -0.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881    0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670    1.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9739    2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5536    2.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7266    2.8210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216    2.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7441    1.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0466   -0.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3280   -0.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157   -0.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6207   -1.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3440   -1.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0534   -1.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2315    1.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0587    1.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4745    2.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0677    2.8551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2404    2.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8201    2.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085   -1.7700    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.4862    3.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
  6  7  2  0
 13 14  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA1093562

   2-(4-Fluorophenyl)-4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-3-(pyridin-4-yl)-1H-pyrrole

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: 333.41

Molecular Weight (Monoisotopic): 333.1641

AlogP: 4.60

#Rotatable Bonds: 3

Polar Surface Area: 31.92

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.69

CX LogP: 3.57

CX LogD: 2.26

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: -0.41

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