N-(2-(dimethylamino)-7-(piperidin-1-yl)quinolin-6-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

ID: ALA4551768

PubChem CID: 155555362

Max Phase: Preclinical

Molecular Formula: C23H25N7O

Molecular Weight: 415.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc2cc(NC(=O)c3cnn4cccnc34)c(N3CCCCC3)cc2n1

Standard InChI:  InChI=1S/C23H25N7O/c1-28(2)21-8-7-16-13-19(20(14-18(16)26-21)29-10-4-3-5-11-29)27-23(31)17-15-25-30-12-6-9-24-22(17)30/h6-9,12-15H,3-5,10-11H2,1-2H3,(H,27,31)

Standard InChI Key:  AHYTYKPDDJPJKK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   22.1701  -10.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1689  -11.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8770  -11.4145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8752   -9.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5838  -10.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5845  -11.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2931  -11.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0013  -10.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9966  -10.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2875   -9.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7018   -9.7626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6968   -8.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4021   -8.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9867   -8.5411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2812   -7.5428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4830   -7.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6942   -8.2481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1529   -8.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4089   -9.6262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2057   -9.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7460   -9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4872   -8.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7106  -11.4035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7095  -12.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4147  -12.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1233  -12.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1221  -11.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4123  -10.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4605  -11.4090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7533  -10.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4618  -12.2249    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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 18  2  0
 17 15  1  0
 15 16  2  0
 16 13  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  8 23  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 29 30  1  0
 29 31  1  0
  2 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4551768

   ---

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: 415.50

Molecular Weight (Monoisotopic): 415.2121

AlogP: 3.59

#Rotatable Bonds: 4

Polar Surface Area: 78.66

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.46

CX Basic pKa: 7.79

CX LogP: 3.56

CX LogD: 3.04

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.55

Np Likeness Score: -2.18

References

1. Bryan MC, Drobnick J, Gobbi A, Kolesnikov A, Chen Y, Rajapaksa N, Ndubaku C, Feng J, Chang W, Francis R, Yu C, Choo EF, DeMent K, Ran Y, An L, Emson C, Huang Z, Sujatha-Bhaskar S, Brightbill H, DiPasquale A, Maher J, Wai J, McKenzie BS, Lupardus PJ, Zarrin AA, Kiefer JR..  (2019)  Development of Potent and Selective Pyrazolopyrimidine IRAK4 Inhibitors.,  62  (13): [PMID:31082230] [10.1021/acs.jmedchem.9b00439]

Source

Source(1):

• Scientific Literature