N-(3-(1-Amino-3-methyl-3,4-dihydro-2,7-naphthyridin-3-yl)-4-fluorophenyl)-5-cyanopicolinamide

ID: ALA4876909

PubChem CID: 56968931

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)Cc2ccncc2C(N)=N1

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

Standard InChI Key:  JKGKDTCSFLEUTI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   24.2206   -9.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6361   -9.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2157   -8.4958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6325   -8.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2143   -7.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8098   -9.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8086  -10.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5167  -10.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.9351  -10.5438    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.5157   -7.2543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1018   -8.9061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3939   -9.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6863   -8.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3937  -10.1316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6900   -8.0906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9832   -7.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2744   -8.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2479   -8.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9841   -9.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5753   -7.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8743   -7.2490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9410   -7.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6325   -7.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3066   -7.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2905   -6.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5945   -6.1065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9232   -6.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  4  1  1  0
  4  6  2  0
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  5 26  1  0
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  7  8  2  0
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  9 10  2  0
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  2 11  2  0
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  6 13  1  0
  7 14  1  0
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 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4876909

   N-[3-(1-amino-3-methyl-4H-2,7-naphthyridin-3-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: 7.74

CX LogP: 2.26

CX LogD: 1.76

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.70

Np Likeness Score: -1.47

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