(R)-8-amino-2-(4-methylcyclohexyl)-5-(4-((2-methylpyrrolidin-1-yl)methyl)phenyl)-3,4-dihydro-2,7-naphthyridin-1(2H)-one

ID: ALA5209509

PubChem CID: 168296398

Max Phase: Preclinical

Molecular Formula: C27H36N4O

Molecular Weight: 432.61

Names and Identifiers

Canonical SMILES:  CC1CCC(N2CCc3c(-c4ccc(CN5CCC[C@H]5C)cc4)cnc(N)c3C2=O)CC1

Standard InChI:  InChI=1S/C27H36N4O/c1-18-5-11-22(12-6-18)31-15-13-23-24(16-29-26(28)25(23)27(31)32)21-9-7-20(8-10-21)17-30-14-3-4-19(30)2/h7-10,16,18-19,22H,3-6,11-15,17H2,1-2H3,(H2,28,29)/t18?,19-,22?/m1/s1

Standard InChI Key:  QPRFLHHDQOLCJS-GSVIPDFHSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   -3.2267    1.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9411    1.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9411    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2267   -0.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5121    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5121    1.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7976   -0.0159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0832    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3687   -0.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3687   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0832   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0832   -2.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3687   -2.4910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458   -2.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0602   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0602   -0.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7747    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4892   -0.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2037    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2037    1.2215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5362    1.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912    2.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6162    2.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8712    1.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6558    1.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4892   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7747   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7976   -2.4910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7976   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5121   -1.2535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6558    1.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  9  8  1  0
 10  9  1  0
 11 10  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 10 15  1  0
 16 15  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 19 20  1  0
 20 21  1  0
 22 21  1  0
 22 23  1  0
 23 24  1  0
 25 24  1  0
 21 25  1  0
 25 26  1  1
 27 19  1  0
 28 27  2  0
 16 28  1  0
 12 29  1  0
 30 11  1  0
  7 30  1  0
 30 31  2  0
  2 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5209509

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 432.61

Molecular Weight (Monoisotopic): 432.2889

AlogP: 4.89

#Rotatable Bonds: 4

Polar Surface Area: 62.46

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.82

CX LogP: 5.01

CX LogD: 2.61

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.75

Np Likeness Score: -0.38

References

1. Witten MR, Wu L, Lai CT, Kapilashrami K, Pusey M, Gallagher K, Chen Y, Yao W..  (2022)  Inhibition of ALK2 with bicyclic pyridyllactams.,  55  [PMID:34780900] [10.1016/j.bmcl.2021.128452]

Source

Source(1):

• Scientific Literature