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

ID: ALA5209497

PubChem CID: 168296388

Max Phase: Preclinical

Molecular Formula: C27H35FN4O

Molecular Weight: 450.60

Names and Identifiers

Canonical SMILES:  CC1CCC(N2CCc3c(-c4ccc(CN5CCC[C@H]5C)c(F)c4)cnc(N)c3C2=O)CC1

Standard InChI:  InChI=1S/C27H35FN4O/c1-17-5-9-21(10-6-17)32-13-11-22-23(15-30-26(29)25(22)27(32)33)19-7-8-20(24(28)14-19)16-31-12-3-4-18(31)2/h7-8,14-15,17-18,21H,3-6,9-13,16H2,1-2H3,(H2,29,30)/t17?,18-,21?/m1/s1

Standard InChI Key:  NCSOXYHHFXDNEU-IDYZSHNDSA-N

Molfile:  

 
     RDKit          2D

 33 37  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
    1.7747    1.2215    0.0000 F   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
 18 19  1  0
 20 18  2  0
 20 21  1  0
 21 22  1  0
 23 22  1  0
 23 24  1  0
 24 25  1  0
 26 25  1  0
 22 26  1  0
 26 27  1  1
 28 20  1  0
 29 28  2  0
 16 29  1  0
 12 30  1  0
 31 11  1  0
  7 31  1  0
 31 32  2  0
  2 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5209497

   ---

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: 450.60

Molecular Weight (Monoisotopic): 450.2795

AlogP: 5.03

#Rotatable Bonds: 4

Polar Surface Area: 62.46

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.72

CX LogP: 5.15

CX LogD: 3.81

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.71

Np Likeness Score: -0.66

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