N-(3-(8-Amino-6-methyl-5,6-dihydro-1,7-naphthyridin-6-yl)-4-fluorophenyl)-5-cyanopicolinamide

ID: ALA4878232

PubChem CID: 89759654

Max Phase: Preclinical

Molecular Formula: C22H17FN6O

Molecular Weight: 400.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(c2cc(NC(=O)c3ccc(C#N)cn3)ccc2F)Cc2cccnc2C(N)=N1

Standard InChI:  InChI=1S/C22H17FN6O/c1-22(10-14-3-2-8-26-19(14)20(25)29-22)16-9-15(5-6-17(16)23)28-21(30)18-7-4-13(11-24)12-27-18/h2-9,12H,10H2,1H3,(H2,25,29)(H,28,30)

Standard InChI Key:  QIEFQYLCHKYOIE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   15.8925   -8.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1861   -9.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6015   -9.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1812   -8.3431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5980   -8.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1798   -7.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7753   -9.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7741   -9.9819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4822  -10.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1918   -9.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4804   -8.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9006  -10.3911    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.4812   -7.1016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0672   -8.7533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3594   -9.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6518   -8.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3592   -9.9789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6555   -7.9379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9487   -7.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2399   -7.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2134   -8.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9496   -9.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5408   -7.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8398   -7.0963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9065   -7.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5980   -7.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2721   -7.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2560   -6.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5600   -5.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8887   -6.3640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  4  1  1  0
  4  6  2  0
  1  5  1  0
  5 26  1  0
 25  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  2  1  0
  2 11  2  0
 11  7  1  0
 10 12  1  0
  6 13  1  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 16  1  0
 23 24  3  0
 20 23  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878232

   N-[3-(8-amino-6-methyl-5H-1,7-naphthyridin-6-yl)-4-fluorophenyl]-5-cyanopyridine-2-carboxamide

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: 400.42

Molecular Weight (Monoisotopic): 400.1448

AlogP: 2.92

#Rotatable Bonds: 3

Polar Surface Area: 117.05

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.93

CX Basic pKa: 6.44

CX LogP: 2.65

CX LogD: 2.60

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.70

Np Likeness Score: -1.50

References

1. Nakahara K, Mitsuoka Y, Kasuya S, Yamamoto T, Yamamoto S, Ito H, Kido Y, Kusakabe KI..  (2021)  Balancing potency and basicity by incorporating fluoropyridine moieties: Discovery of a 1-amino-3,4-dihydro-2,6-naphthyridine BACE1 inhibitor that affords robust and sustained central Aβ reduction.,  216  [PMID:33765486] [10.1016/j.ejmech.2021.113270]

Source

Source(1):

• Scientific Literature