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

ID: ALA1092617

PubChem CID: 9928889

Max Phase: Preclinical

Molecular Formula: C23H24FN3

Molecular Weight: 361.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1CC=C(c2c[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1

Standard InChI:  InChI=1S/C23H24FN3/c1-2-13-27-14-9-17(10-15-27)21-16-26-23(19-3-5-20(24)6-4-19)22(21)18-7-11-25-12-8-18/h3-9,11-12,16,26H,2,10,13-15H2,1H3

Standard InChI Key:  XGLAAPICLZABCU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -2.0328   -8.6381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816   -8.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6605   -7.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4845   -7.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9054   -6.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4987   -5.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9187   -5.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7453   -5.2552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1501   -5.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7278   -6.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4255   -8.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1437   -8.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8556   -8.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8506   -9.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1277   -9.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -9.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2417   -6.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150   -6.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -5.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4060   -5.2211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2328   -5.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6529   -5.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5624   -9.8437    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0123   -4.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8381   -4.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2565   -3.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
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  1 12  1  0
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  8  9  2  0
  4  5  1  0
  9 10  1  0
  5  1  2  0
 10 11  2  0
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 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
 25 26  1  0
 12 13  2  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1092617

   4-[2-(4-fluorophenyl)-4-(1-propyl-3,6-dihydro-2H-pyridin-4-yl)-1H-pyrrol-3-yl]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: 361.46

Molecular Weight (Monoisotopic): 361.1954

AlogP: 5.38

#Rotatable Bonds: 5

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: 9.26

CX LogP: 4.45

CX LogD: 2.59

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -0.68

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