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

ID: ALA1093563

PubChem CID: 9798352

Max Phase: Preclinical

Molecular Formula: C22H22FN3

Molecular Weight: 347.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CC=C(c2c[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1

Standard InChI:  InChI=1S/C22H22FN3/c1-2-26-13-9-16(10-14-26)20-15-25-22(18-3-5-19(23)6-4-18)21(20)17-7-11-24-12-8-17/h3-9,11-12,15,25H,2,10,13-14H2,1H3

Standard InChI Key:  JTNDMLYOUULPRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   11.5151   -0.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1969   -0.6386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8483   -0.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5692    0.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7451    0.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3241    1.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7309    2.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3108    2.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4839    2.7451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0790    2.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5015    1.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8038   -0.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0854   -0.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3734   -0.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3784   -1.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1015   -1.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8106   -1.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9882    1.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8151    1.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2308    2.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8241    2.7793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9971    2.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5768    2.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6664   -1.8446    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.2425    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0685    3.4850    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
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093563

   4-[4-(1-ethyl-3,6-dihydro-2H-pyridin-4-yl)-2-(4-fluorophenyl)-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: 347.44

Molecular Weight (Monoisotopic): 347.1798

AlogP: 4.99

#Rotatable Bonds: 4

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: 8.96

CX LogP: 3.93

CX LogD: 2.36

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -0.60

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