rac-2-(2-amino-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-3-yloxy)-2-(2,6-dichloro-3-fluorophenyl)ethanol

ID: ALA4741011

PubChem CID: 162645446

Max Phase: Preclinical

Molecular Formula: C21H22Cl2FN5O2

Molecular Weight: 466.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncc(-c2cnn(C3CCNCC3)c2)cc1OC(CO)c1c(Cl)ccc(F)c1Cl

Standard InChI:  InChI=1S/C21H22Cl2FN5O2/c22-15-1-2-16(24)20(23)19(15)18(11-30)31-17-7-12(8-27-21(17)25)13-9-28-29(10-13)14-3-5-26-6-4-14/h1-2,7-10,14,18,26,30H,3-6,11H2,(H2,25,27)

Standard InChI Key:  AADFAKZRNCLPGT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   18.0064  -17.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0051  -17.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7200  -18.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4363  -17.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4335  -17.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7182  -16.7492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2908  -18.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5374  -18.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3969  -19.3898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2039  -19.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1515  -18.4002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1528  -19.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8679  -19.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8645  -20.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5788  -20.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2935  -20.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2896  -19.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5747  -19.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4390  -19.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5688  -18.3946    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.1495  -20.8702    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.0019  -19.2110    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.1464  -16.7431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9786  -18.6702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1543  -18.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8229  -17.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0065  -17.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5156  -18.3967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8469  -19.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6693  -19.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7238  -19.2274    0.0000 O   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 24  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
 12 19  1  0
 18 20  1  0
 14 21  1  0
 17 22  1  0
  5 23  1  0
  9 24  1  0
 25 26  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 24 25  1  0
 19 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741011

   ---

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: 466.34

Molecular Weight (Monoisotopic): 465.1135

AlogP: 4.01

#Rotatable Bonds: 6

Polar Surface Area: 98.22

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.12

CX LogP: 2.53

CX LogD: -0.09

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: -0.70

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