Rac-N-((5,5-difluoropiperidin-3-yl)methyl)-7-(6-(dimethylamino)pyridin-3-yl)pyrido[4,3-b]pyrazin-5-amine

ID: ALA4571227

PubChem CID: 68310172

Max Phase: Preclinical

Molecular Formula: C20H23F2N7

Molecular Weight: 399.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(-c2cc3nccnc3c(NCC3CNCC(F)(F)C3)n2)cn1

Standard InChI:  InChI=1S/C20H23F2N7/c1-29(2)17-4-3-14(11-26-17)15-7-16-18(25-6-5-24-16)19(28-15)27-10-13-8-20(21,22)12-23-9-13/h3-7,11,13,23H,8-10,12H2,1-2H3,(H,27,28)

Standard InChI Key:  MDZNNHJKFFMBHO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   29.9900  -11.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7049  -12.0239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7031  -10.3709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4184  -10.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4193  -11.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1345  -12.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8496  -11.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8448  -10.7731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1289  -10.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5621  -12.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5639  -12.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2792  -13.2445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.9931  -12.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9872  -11.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2714  -11.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1246   -9.5408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7097  -13.2379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7140  -14.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4221  -12.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8368   -9.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5535   -9.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5532  -10.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2658  -10.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9805  -10.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9781   -9.5249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2609   -9.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6761  -11.3461    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   34.8469  -11.3461    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
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  9 10  2  0
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 11 12  2  0
 12 13  1  0
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 14 15  1  0
 15 16  2  0
 16 11  1  0
  8 11  1  0
 10 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 24 28  1  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4571227

   N-[(5,5-difluoropiperidin-3-yl)methyl]-7-[6-(dimethylamino)pyridin-3-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: 399.45

Molecular Weight (Monoisotopic): 399.1983

AlogP: 2.81

#Rotatable Bonds: 5

Polar Surface Area: 78.86

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.99

CX LogP: 1.84

CX LogD: 1.70

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -0.94

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