5-(2-(2-azabicyclo[2.1.1]hexan-2-yl)-6-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)pyrimidin-4-yl)pyrazin-2-amine

ID: ALA5281886

Max Phase: Preclinical

Molecular Formula: C18H21N7O

Molecular Weight: 351.41

Names and Identifiers

Canonical SMILES:  Nc1cnc(-c2cc(N3C[C@@H]4C[C@H]3CO4)nc(N3CC4CC3C4)n2)cn1

Standard InChI:  InChI=1S/C18H21N7O/c19-16-6-20-15(5-21-16)14-4-17(24-8-13-3-12(24)9-26-13)23-18(22-14)25-7-10-1-11(25)2-10/h4-6,10-13H,1-3,7-9H2,(H2,19,21)/t10?,11?,12-,13-/m0/s1

Standard InChI Key:  XGFVOKJJQCQLJX-TYUFSLCMSA-N

Molfile:  

 
     RDKit          2D

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   -1.3641   -2.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2086   -2.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7912   -1.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250   -1.0144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0777   -1.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3641   -1.8539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6505   -1.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6505   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0614   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7741   -0.6168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7741   -1.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4877   -1.8503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5738   -2.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795   -2.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912   -2.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2401   -1.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9858   -1.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0603   -1.8505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0614    0.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539    1.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539    1.8541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0595    2.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0595    3.0898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7704    1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7704    1.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7912   -2.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0777   -3.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9  8  2  0
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 13 12  1  0
 14 13  1  0
 15 14  1  0
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 14 18  1  0
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  8 19  1  0
 19 12  2  0
 10 20  1  0
 21 20  2  0
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 23 22  2  0
 23 24  1  0
 25 23  1  0
 20 26  1  0
 26 25  2  0
  4 27  1  0
 27 28  1  0
 28  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281886

   ---

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: 351.41

Molecular Weight (Monoisotopic): 351.1808

AlogP: 1.09

#Rotatable Bonds: 3

Polar Surface Area: 93.29

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.90

CX LogP: 1.43

CX LogD: 1.43

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.88

Np Likeness Score: -0.23

References

1. Craig RA, Fox BM, Hu C, Lexa KW, Osipov M, Thottumkara AP, Larhammar M, Miyamoto T, Rana A, Kane LA, Yulyaningsih E, Solanoy H, Nguyen H, Chau R, Earr T, Kajiwara Y, Fleck D, Lucas A, Haddick PCG, Takahashi RH, Tong V, Wang J, Canet MJ, Poda SB, Scearce-Levie K, Srivastava A, Sweeney ZK, Xu M, Zhang R, He J, Lei Y, Zhuo Z, de Vicente J..  (2022)  Discovery of Potent and Selective Dual Leucine Zipper Kinase/Leucine Zipper-Bearing Kinase Inhibitors with Neuroprotective Properties in In Vitro and In Vivo Models of Amyotrophic Lateral Sclerosis.,  65  (24.0): [PMID:36469401] [10.1021/acs.jmedchem.2c01056]

Source

Source(1):

• Scientific Literature