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

ID: ALA1091626

PubChem CID: 9820331

Max Phase: Preclinical

Molecular Formula: C23H24FN3

Molecular Weight: 361.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CCC(c2c[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)=CC1C

Standard InChI:  InChI=1S/C23H24FN3/c1-3-27-13-10-19(14-16(27)2)21-15-26-23(18-4-6-20(24)7-5-18)22(21)17-8-11-25-12-9-17/h4-9,11-12,14-16,26H,3,10,13H2,1-2H3

Standard InChI Key:  ASPRKFLJNYTNON-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.1503  -25.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8319  -25.6049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4832  -25.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2042  -24.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3803  -24.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9593  -23.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3660  -22.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9460  -22.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1194  -22.2220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7146  -22.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1369  -23.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4392  -25.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7210  -25.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0091  -25.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0141  -26.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7370  -26.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4460  -26.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6230  -23.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4497  -23.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8653  -22.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4587  -22.1879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6319  -22.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2118  -22.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3023  -26.8105    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.8770  -21.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6910  -22.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7028  -21.4822    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
 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
M  END

Alternative Forms

1. Parent:

   

   ALA1091626

   4-[4-(1-ethyl-6-methyl-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: 361.46

Molecular Weight (Monoisotopic): 361.1954

AlogP: 5.38

#Rotatable Bonds: 4

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: 9.24

CX LogP: 4.34

CX LogD: 2.50

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: -0.33

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