(S)-7-(6-(dimethylamino)pyridin-3-yl)-N-(piperidin-3-ylmethyl)pyrido[4,3-b]pyrazin-5-amine

ID: ALA4528289

PubChem CID: 66555698

Max Phase: Preclinical

Molecular Formula: C20H25N7

Molecular Weight: 363.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(-c2cc3nccnc3c(NC[C@H]3CCCNC3)n2)cn1

Standard InChI:  InChI=1S/C20H25N7/c1-27(2)18-6-5-15(13-24-18)16-10-17-19(23-9-8-22-17)20(26-16)25-12-14-4-3-7-21-11-14/h5-6,8-10,13-14,21H,3-4,7,11-12H2,1-2H3,(H,25,26)/t14-/m0/s1

Standard InChI Key:  CLKZDZYGBHNPSM-AWEZNQCLSA-N

Molfile:  

 
     RDKit          2D

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   12.0377  -17.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0366  -18.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7446  -18.4431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7428  -16.8058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4514  -17.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4522  -18.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1607  -18.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8690  -18.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8643  -17.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1552  -16.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5747  -18.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5766  -19.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2850  -19.6521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9921  -19.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9863  -18.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2773  -18.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1508  -15.9836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7020  -19.6456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7062  -20.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4075  -19.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8564  -15.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5662  -15.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5659  -16.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2717  -17.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9797  -16.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9773  -15.9679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2670  -15.5586    0.0000 C   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
 11 12  2  0
 12 13  1  0
 13 14  2  0
 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
 22 21  1  6
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4528289

   7-[6-(Dimethylamino)pyridin-3-Yl]-~{n}-[[(3~{s})-Piperidin-3-Yl]methyl]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: 363.47

Molecular Weight (Monoisotopic): 363.2171

AlogP: 2.56

#Rotatable Bonds: 5

Polar Surface Area: 78.86

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.17

CX LogP: 1.81

CX LogD: -0.84

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -1.08

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