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

ID: ALA1091932

PubChem CID: 9864420

Max Phase: Preclinical

Molecular Formula: C24H26FN3

Molecular Weight: 375.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1CCC(c2c[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)=CC1C

Standard InChI:  InChI=1S/C24H26FN3/c1-3-13-28-14-10-20(15-17(28)2)22-16-27-24(19-4-6-21(25)7-5-19)23(22)18-8-11-26-12-9-18/h4-9,11-12,15-17,27H,3,10,13-14H2,1-2H3

Standard InChI Key:  KSSRXIYWMVGMKJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   18.8067  -24.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4882  -25.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1395  -24.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8605  -23.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0366  -24.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6157  -23.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0224  -22.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6024  -21.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7758  -21.8839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3710  -22.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7933  -23.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0956  -25.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3774  -24.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6655  -25.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6705  -26.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3934  -26.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1024  -26.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2793  -23.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1060  -23.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5216  -22.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1150  -21.8498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2882  -21.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8681  -22.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9587  -26.4724    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.5333  -21.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3473  -22.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3592  -21.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7776  -20.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 20 26  1  0
 12 13  2  0
 25 27  1  0
  6  7  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091932

   4-[2-(4-fluorophenyl)-4-(6-methyl-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: 375.49

Molecular Weight (Monoisotopic): 375.2111

AlogP: 5.77

#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: 9.54

CX LogP: 4.87

CX LogD: 2.74

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -0.39

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