2-acetamido-N-(5-((1-(4-fluorobenzyl)piperidin-4-yl)methoxy)pyridin-3-yl)isonicotinamide

ID: ALA4875903

PubChem CID: 164628497

Max Phase: Preclinical

Molecular Formula: C26H28FN5O3

Molecular Weight: 477.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc(C(=O)Nc2cncc(OCC3CCN(Cc4ccc(F)cc4)CC3)c2)ccn1

Standard InChI:  InChI=1S/C26H28FN5O3/c1-18(33)30-25-12-21(6-9-29-25)26(34)31-23-13-24(15-28-14-23)35-17-20-7-10-32(11-8-20)16-19-2-4-22(27)5-3-19/h2-6,9,12-15,20H,7-8,10-11,16-17H2,1H3,(H,31,34)(H,29,30,33)

Standard InChI Key:  IGURROANDGIDJI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   10.9365  -32.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6549  -33.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3714  -32.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3808  -31.8416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6608  -31.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9338  -31.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0963  -31.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0963  -30.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8149  -30.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8247  -29.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1067  -28.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3799  -29.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3819  -30.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8007  -33.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5014  -32.7135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2316  -33.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0793  -32.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792  -33.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4041  -34.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1351  -34.4020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8324  -33.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6533  -32.7974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9524  -33.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2266  -32.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2033  -32.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4783  -31.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7764  -32.0601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041  -32.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5295  -33.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1048  -33.3239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775  -32.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6849  -33.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3496  -32.1126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9773  -34.0546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1115  -28.1142    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 14 15  1  0
 15 16  1  0
 16  1  1  0
 14 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 14  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 23 34  2  0
 11 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875903

   ---

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: 477.54

Molecular Weight (Monoisotopic): 477.2176

AlogP: 4.12

#Rotatable Bonds: 8

Polar Surface Area: 96.45

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.06

CX Basic pKa: 8.29

CX LogP: 2.66

CX LogD: 1.72

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.51

Np Likeness Score: -1.80

References

1. Jiang X, Liu C, Zou M, Xie H, Lin T, Lyu W, Xu J, Li Y, Feng F, Sun H, Liu W..  (2021)  Discovery of 2-(cyclopropanecarboxamido)-N-(5-((1-(4-fluorobenzyl)piperidin-4-yl)methoxy)pyridin-3-yl)isonicotinamide as a potent dual AChE/GSK3β inhibitor for the treatment of Alzheimer's disease: Significantly increasing the level of acetylcholine in the brain without affecting that in intestine.,  223  [PMID:34198150] [10.1016/j.ejmech.2021.113663]

Source

Source(1):

• Scientific Literature