(S)-N-(3-(1-amino-5-fluoro-3-methyl-3,4-dihydro-2,6-naphthyridin-3-yl)-4-fluorophenyl)-5-cyanopicolinamide

ID: ALA4868952

PubChem CID: 164619763

Max Phase: Preclinical

Molecular Formula: C22H16F2N6O

Molecular Weight: 418.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@]1(c2cc(NC(=O)c3ccc(C#N)cn3)ccc2F)Cc2c(ccnc2F)C(N)=N1

Standard InChI:  InChI=1S/C22H16F2N6O/c1-22(9-15-14(20(26)30-22)6-7-27-19(15)24)16-8-13(3-4-17(16)23)29-21(31)18-5-2-12(10-25)11-28-18/h2-8,11H,9H2,1H3,(H2,26,30)(H,29,31)/t22-/m0/s1

Standard InChI Key:  RLVDCTMTAOERIM-QFIPXVFZSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   18.5628  -19.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8565  -20.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2719  -20.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8515  -19.2472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2683  -19.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8501  -18.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4456  -20.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4444  -20.8861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1525  -21.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8621  -20.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1507  -19.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5709  -21.2953    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.1516  -18.0057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7376  -19.6575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0297  -20.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3221  -19.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0295  -20.8831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3258  -18.8420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6191  -18.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9103  -18.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8837  -19.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6200  -20.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2112  -18.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5101  -18.0004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5768  -18.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2683  -18.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9424  -18.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9263  -17.2376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2303  -16.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5591  -17.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6582  -18.4229    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  6
  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
 27 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4868952

   ---

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: 418.41

Molecular Weight (Monoisotopic): 418.1354

AlogP: 3.06

#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: 7.79

CX LogP: 2.80

CX LogD: 2.26

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.63

Np Likeness Score: -1.35

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