3-(2-chlorobenzyloxy)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine

ID: ALA4778070

PubChem CID: 162644472

Max Phase: Preclinical

Molecular Formula: C20H22ClN5O

Molecular Weight: 383.88

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncc(-c2cnn(C3CCNCC3)c2)cc1OCc1ccccc1Cl

Standard InChI:  InChI=1S/C20H22ClN5O/c21-18-4-2-1-3-14(18)13-27-19-9-15(10-24-20(19)22)16-11-25-26(12-16)17-5-7-23-8-6-17/h1-4,9-12,17,23H,5-8,13H2,(H2,22,24)

Standard InChI Key:  BQNKOSUUCJKPPW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    5.7313  -16.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7302  -16.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4382  -17.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1479  -16.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1450  -16.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4364  -15.7575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225  -17.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2762  -17.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1370  -18.3732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9364  -18.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8562  -17.3929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8575  -18.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5658  -18.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5625  -19.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2700  -19.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9781  -19.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9742  -18.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2661  -18.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8512  -15.7515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7228  -17.6604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9061  -17.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5779  -16.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7693  -16.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829  -17.3895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111  -18.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4257  -18.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2601  -17.3874    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8 20  1  0
  9 10  2  0
 10  7  1  0
  2  7  1  0
  4 11  1  0
 11 12  1  0
 12 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
  5 19  1  0
  9 20  1  0
 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 20 21  1  0
 18 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4778070

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 383.88

Molecular Weight (Monoisotopic): 383.1513

AlogP: 3.68

#Rotatable Bonds: 5

Polar Surface Area: 77.99

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.12

CX LogP: 2.41

CX LogD: -0.21

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -1.06

References

1. May-Dracka TL,Arduini R,Bertolotti-Ciarlet A,Bhisetti G,Brickelmaier M,Cahir-McFarland E,Enyedy I,Fontenot JD,Hesson T,Little K,Lyssikatos J,Marcotte D,McKee T,Murugan P,Patterson T,Peng H,Rushe M,Silvian L,Spilker K,Wu P,Xin Z,Burkly LC.  (2018)  Investigating small molecules to inhibit germinal center kinase-like kinase (GLK/MAP4K3) upstream of PKCθ phosphorylation: Potential therapy to modulate T cell dependent immunity.,  28  (10): [PMID:29636220] [10.1016/j.bmcl.2018.03.032]

Source

Source(1):

• Scientific Literature