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

ID: ALA4794231

PubChem CID: 162672478

Max Phase: Preclinical

Molecular Formula: C22H22Cl2FN5O3

Molecular Weight: 494.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C(Oc1cc(-c2cnn(C3CCNCC3)c2)cnc1N)c1c(Cl)ccc(F)c1Cl

Standard InChI:  InChI=1S/C22H22Cl2FN5O3/c1-32-22(31)20(18-15(23)2-3-16(25)19(18)24)33-17-8-12(9-28-21(17)26)13-10-29-30(11-13)14-4-6-27-7-5-14/h2-3,8-11,14,20,27H,4-7H2,1H3,(H2,26,28)

Standard InChI Key:  XUTRAIFRJXUIET-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    5.4400  -17.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4389  -18.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1536  -18.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8701  -18.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8672  -17.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1519  -16.9157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7245  -18.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9711  -18.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8306  -19.5564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6376  -19.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852  -18.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5864  -19.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3016  -19.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2982  -20.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0125  -21.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7272  -20.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7233  -19.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0084  -19.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8727  -19.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0024  -18.5612    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.5832  -21.0367    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.4356  -19.3776    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5801  -16.9096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4124  -18.8368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5880  -18.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567  -17.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4403  -17.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9492  -18.5633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807  -19.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1030  -19.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8740  -20.6302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1576  -19.3939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4438  -19.8075    0.0000 C   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  2  0
 19 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4794231

   ---

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: 494.35

Molecular Weight (Monoisotopic): 493.1084

AlogP: 4.19

#Rotatable Bonds: 6

Polar Surface Area: 104.29

Molecular Species: BASE

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.12

CX LogP: 2.99

CX LogD: 0.37

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.39

Np Likeness Score: -0.91

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