2-(3-(1-(2-Aminopyrimidin-4-yl)-1H-pyrrolo[3,2-c]pyridin-6-yl)-bicyclo(1.1.1)pentan-1-yl)propan-2-ol

ID: ALA5281273

Max Phase: Preclinical

Molecular Formula: C19H21N5O

Molecular Weight: 335.41

Names and Identifiers

Canonical SMILES:  CC(C)(O)C12CC(c3cc4c(ccn4-c4ccnc(N)n4)cn3)(C1)C2

Standard InChI:  InChI=1S/C19H21N5O/c1-17(2,25)19-9-18(10-19,11-19)14-7-13-12(8-22-14)4-6-24(13)15-3-5-21-16(20)23-15/h3-8,25H,9-11H2,1-2H3,(H2,20,21,23)

Standard InChI Key:  DRKVDJFSVUOKPM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   23.4496   -8.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8642   -9.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2746   -8.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7386  -12.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4498  -11.6170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4495  -10.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7358  -10.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0257  -11.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0275  -10.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2416  -10.5354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7582  -11.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2427  -11.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9917   -9.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5401   -9.1483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2869   -8.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4841   -8.1934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9349   -8.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1885   -9.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1592  -10.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9488  -10.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3646   -9.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5806   -9.7880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7446  -10.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1717   -9.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8392   -7.7559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  6 19  1  0
 19 20  1  0
 20 24  1  0
 24 21  1  0
 21 19  1  0
 24  2  1  0
  2 22  1  0
 19 23  1  0
 23 24  1  0
 15 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281273

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 335.41

Molecular Weight (Monoisotopic): 335.1746

AlogP: 2.59

#Rotatable Bonds: 3

Polar Surface Area: 89.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.29

CX LogP: 2.26

CX LogD: 2.01

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: -0.31

References

1. Halkina T, Henderson JL, Lin EY, Himmelbauer MK, Jones JH, Nevalainen M, Feng J, King K, Rooney M, Johnson JL, Marcotte DJ, Chodaparambil JV, Kumar PR, Patterson TA, Murugan P, Schuman E, Wong L, Hesson T, Lamore S, Bao C, Calhoun M, Certo H, Amaral B, Dillon GM, Gilfillan R, de Turiso FG..  (2021)  Discovery of Potent and Brain-Penetrant Tau Tubulin Kinase 1 (TTBK1) Inhibitors that Lower Tau Phosphorylation In Vivo.,  64  (9.0): [PMID:33944571] [10.1021/acs.jmedchem.1c00382]

Source

Source(1):

• Scientific Literature