Rac-N-((5,5-difluoropiperidin-3-yl)methyl)-7-(1-methyl-1H-pyrazol-4-yl)pyrido[4,3-b]pyrazin-5-amine

ID: ALA4520397

PubChem CID: 68309298

Max Phase: Preclinical

Molecular Formula: C17H19F2N7

Molecular Weight: 359.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1cc(-c2cc3nccnc3c(NCC3CNCC(F)(F)C3)n2)cn1

Standard InChI:  InChI=1S/C17H19F2N7/c1-26-9-12(8-24-26)13-4-14-15(22-3-2-21-14)16(25-13)23-7-11-5-17(18,19)10-20-6-11/h2-4,8-9,11,20H,5-7,10H2,1H3,(H,23,25)

Standard InChI Key:  QAPDXRHCCUUBNB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   28.5314   -9.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5303  -10.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2451  -10.4942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2434   -8.8413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9587   -9.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9594  -10.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6748  -10.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3898  -10.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3850   -9.2435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6691   -8.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6648   -8.0112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3770   -7.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0937   -8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0933   -8.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8058   -9.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5206   -8.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5182   -7.9954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8011   -7.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1106  -10.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2000  -11.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0076  -11.4733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.4173  -10.7572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8629  -10.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3460  -12.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2162   -9.8166    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.3870   -9.8166    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 10 11  1  0
 11 12  1  0
 13 12  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 19  1  0
  8 19  1  0
 21 24  1  0
 15 25  1  0
 15 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4520397

   N-[(5,5-difluoropiperidin-3-yl)methyl]-7-(1-methylpyrazol-4-yl)pyrido[3,4-b]pyrazin-5-amine

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: 359.38

Molecular Weight (Monoisotopic): 359.1670

AlogP: 2.08

#Rotatable Bonds: 4

Polar Surface Area: 80.55

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.97

CX LogP: 0.78

CX LogD: 0.64

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: -1.13

References

1. Garton NS, Barker MD, Davis RP, Douault C, Hooper-Greenhill E, Jones E, Lewis HD, Liddle J, Lugo D, McCleary S, Preston AGS, Ramirez-Molina C, Neu M, Shipley TJ, Somers DO, Watson RJ, Wilson DM..  (2016)  Optimisation of a novel series of potent and orally bioavailable azanaphthyridine SYK inhibitors.,  26  (19): [PMID:27578246] [10.1016/j.bmcl.2016.08.070]

Source

Source(1):

• Scientific Literature