(S)-3-methyl-5-(piperidin-3-ylmethylamino)-7-p-tolylpyrido[4,3-d]pyrimidin-4(3H)-one

ID: ALA4526150

PubChem CID: 155544000

Max Phase: Preclinical

Molecular Formula: C21H25N5O

Molecular Weight: 363.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2cc3ncn(C)c(=O)c3c(NC[C@H]3CCCNC3)n2)cc1

Standard InChI:  InChI=1S/C21H25N5O/c1-14-5-7-16(8-6-14)17-10-18-19(21(27)26(2)13-24-18)20(25-17)23-12-15-4-3-9-22-11-15/h5-8,10,13,15,22H,3-4,9,11-12H2,1-2H3,(H,23,25)/t15-/m0/s1

Standard InChI Key:  HQXRVTFLFJNGAV-HNNXBMFYSA-N

Molfile:  

 
     RDKit          2D

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   12.7476  -16.6781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7464  -17.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4545  -17.9066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4527  -16.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1613  -16.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1621  -17.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8706  -17.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5789  -17.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5741  -16.6676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8650  -16.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2846  -17.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2865  -18.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9949  -19.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7020  -18.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6962  -17.8828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9872  -17.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8607  -15.4471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5662  -15.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2761  -15.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2758  -16.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9816  -16.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6895  -16.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6872  -15.4314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9768  -15.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4118  -19.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4503  -15.4520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0398  -16.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  1  0
  5  6  2  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  6
 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
  4 26  2  0
  1 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4526150

   ---

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): 363.2059

AlogP: 2.72

#Rotatable Bonds: 4

Polar Surface Area: 71.84

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.17

CX LogP: 3.14

CX LogD: 0.49

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.75

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