Rac-N,N-dimethyl-5-(5-(2-(piperidin-3-yl)ethyl)pyrido[4,3-b]pyrazin-7-yl)pyridin-2-amine

ID: ALA4560963

PubChem CID: 89912923

Max Phase: Preclinical

Molecular Formula: C21H26N6

Molecular Weight: 362.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(-c2cc3nccnc3c(CCC3CCCNC3)n2)cn1

Standard InChI:  InChI=1S/C21H26N6/c1-27(2)20-8-6-16(14-25-20)18-12-19-21(24-11-10-23-19)17(26-18)7-5-15-4-3-9-22-13-15/h6,8,10-12,14-15,22H,3-5,7,9,13H2,1-2H3

Standard InChI Key:  KSJOLPSCOYLXKR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   21.9075  -17.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9064  -18.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6213  -19.0075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6194  -17.3544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3348  -17.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3355  -18.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0509  -19.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7659  -18.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7612  -17.7566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0453  -17.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4785  -18.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4803  -19.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1956  -20.2279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9095  -19.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9035  -18.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1877  -18.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0409  -16.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7532  -16.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4699  -16.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4696  -17.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1821  -17.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8969  -17.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8944  -16.5085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1773  -16.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6261  -20.2214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6304  -21.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3384  -19.8052    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
 17 18  1  0
 19 18  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 14 25  1  0
 25 26  1  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4560963

   N,N-dimethyl-5-[5-(2-piperidin-3-ylethyl)pyrido[3,4-b]pyrazin-7-yl]pyridin-2-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: 362.48

Molecular Weight (Monoisotopic): 362.2219

AlogP: 3.09

#Rotatable Bonds: 5

Polar Surface Area: 66.83

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.49

CX LogP: 2.55

CX LogD: -0.32

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: -0.86

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