Rac-5-((4,4-difluoropiperidin-3-yl)methoxy)-7-(1-methyl-1H-pyrazol-4-yl)pyrido[4,3-b]pyrazine

ID: ALA4561098

PubChem CID: 66556201

Max Phase: Preclinical

Molecular Formula: C17H18F2N6O

Molecular Weight: 360.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1cc(-c2cc3nccnc3c(OCC3CNCCC3(F)F)n2)cn1

Standard InChI:  InChI=1S/C17H18F2N6O/c1-25-9-11(7-23-25)13-6-14-15(22-5-4-21-14)16(24-13)26-10-12-8-20-3-2-17(12,18)19/h4-7,9,12,20H,2-3,8,10H2,1H3

Standard InChI Key:  WFOLLQWDLJNOGD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   28.2188   -2.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2177   -3.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9325   -4.1526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9307   -2.4996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6460   -2.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6468   -3.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3621   -4.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0771   -3.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0724   -2.9018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3564   -2.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3521   -1.6697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0643   -1.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7810   -1.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7807   -2.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4932   -2.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2080   -2.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2055   -1.6538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4884   -1.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7978   -4.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8873   -4.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6949   -5.1317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1047   -4.4156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5501   -3.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0334   -5.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9785   -2.2666    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.5619   -3.2791    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
 14 25  1  0
 14 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4561098

   5-{[(4,4-Difluoro-3-piperidinyl)methyl]oxy}-7-(1-methyl-1H-pyrazol-4-yl)pyrido[3,4-b]pyrazine

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: 360.37

Molecular Weight (Monoisotopic): 360.1510

AlogP: 2.05

#Rotatable Bonds: 4

Polar Surface Area: 77.75

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.10

CX LogP: 1.16

CX LogD: -0.54

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: -0.90

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