5-(6-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridazin-3-yl)-2-(trifluoromethyl)-1H-indole

ID: ALA1083614

PubChem CID: 46891585

Max Phase: Preclinical

Molecular Formula: C19H18F3N5

Molecular Weight: 373.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C[C@@H]2C[C@H]1CN2c1ccc(-c2ccc3[nH]c(C(F)(F)F)cc3c2)nn1

Standard InChI:  InChI=1S/C19H18F3N5/c1-26-9-14-8-13(26)10-27(14)18-5-4-16(24-25-18)11-2-3-15-12(6-11)7-17(23-15)19(20,21)22/h2-7,13-14,23H,8-10H2,1H3/t13-,14-/m0/s1

Standard InChI Key:  PZVTWWKRIHYSCB-KBPBESRZSA-N

Molfile:  

     RDKit          2D

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    5.2471  -20.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0613  -20.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4670  -20.1184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0613  -19.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2471  -19.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8345  -20.1184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2786  -20.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6853  -20.8267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4984  -20.8289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9103  -20.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5001  -19.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6849  -19.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0203  -20.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2408  -20.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2408  -18.5889    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0550  -21.6356    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7353  -20.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9712  -19.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1466  -19.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1491  -20.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3883  -20.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9755  -20.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5292  -21.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2843  -21.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1970  -20.2958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0007  -21.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0015  -22.3572    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.7162  -21.1165    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.7115  -21.9410    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  7  1  0
  6 13  1  0
  5 14  1  0
  2 14  1  0
  5 15  1  1
  2 16  1  1
 17 20  2  0
  1  2  1  0
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  1  6  1  0
 18 19  2  0
 19 17  1  0
 10 17  1  0
 22 20  1  0
  2  3  1  0
 21 22  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  8  2  0
  8  9  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  1  0
  9 10  2  0
 24 26  1  0
 10 11  1  0
 26 27  1  0
 11 12  2  0
 26 28  1  0
 12  7  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1083614

   5-(6-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridazin-3-yl)-2-(trifluoromethyl)-1H-indole

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: 373.38

Molecular Weight (Monoisotopic): 373.1514

AlogP: 3.54

#Rotatable Bonds: 2

Polar Surface Area: 48.05

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.83

CX Basic pKa: 7.69

CX LogP: 3.26

CX LogD: 2.80

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: -1.00

References

1. Li T, Bunnelle WH, Ryther KB, Anderson DJ, Malysz J, Helfrich R, Grønlien JH, Håkerud M, Peters D, Schrimpf MR, Gopalakrishnan M, Ji J..  (2010)  Syntheses and structure-activity relationship (SAR) studies of 2,5-diazabicyclo[2.2.1]heptanes as novel alpha7 neuronal nicotinic receptor (NNR) ligands.,  20  (12): [PMID:20472430] [10.1016/j.bmcl.2010.04.105]

Source

Source(1):

• Scientific Literature