2-((4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)-4-fluoropiperidin-1-yl)methyl)benzonitrile

ID: ALA4867651

PubChem CID: 74539029

Max Phase: Preclinical

Molecular Formula: C25H27FN2O3

Molecular Weight: 422.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C(=O)C(CC1(F)CCN(Cc3ccccc3C#N)CC1)C2

Standard InChI:  InChI=1S/C25H27FN2O3/c1-30-22-12-19-11-20(24(29)21(19)13-23(22)31-2)14-25(26)7-9-28(10-8-25)16-18-6-4-3-5-17(18)15-27/h3-6,12-13,20H,7-11,14,16H2,1-2H3

Standard InChI Key:  FLBIAGQMXSDHGV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   27.5519  -24.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5508  -25.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2656  -25.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2639  -24.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8357  -24.2253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8368  -25.8702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1233  -25.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8302  -23.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9792  -24.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9794  -25.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7699  -25.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2582  -25.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7695  -24.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0242  -23.5873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0785  -26.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4878  -27.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3131  -27.1916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7276  -26.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3167  -25.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4999  -25.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0816  -25.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6732  -25.7628    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.7232  -27.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5481  -27.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9557  -28.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7800  -28.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1957  -27.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7813  -27.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9584  -27.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5430  -29.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1272  -30.0483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 10  2  0
  9  4  2  0
  4  1  1  0
  1  5  1  0
  2  6  1  0
  6  7  1  0
  5  8  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
 13 14  2  0
 12 21  1  0
 20 15  1  0
 20 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 21 20  1  0
 20 22  1  0
 17 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
 30 31  3  0
 25 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4867651

   2-[[4-[(5,6-Dimethoxy-3-oxo-1,2-dihydroinden-2-yl)methyl]-4-fluoropiperidin-1-yl]methyl]benzonitrile

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: 422.50

Molecular Weight (Monoisotopic): 422.2006

AlogP: 4.32

#Rotatable Bonds: 6

Polar Surface Area: 62.56

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.74

CX LogP: 3.49

CX LogD: 3.41

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.69

Np Likeness Score: -0.37

References

1. Zhou Y, Fu Y, Yin W, Li J, Wang W, Bai F, Xu S, Gong Q, Peng T, Hong Y, Zhang D, Zhang D, Liu Q, Xu Y, Xu HE, Zhang H, Jiang H, Liu H..  (2021)  Kinetics-Driven Drug Design Strategy for Next-Generation Acetylcholinesterase Inhibitors to Clinical Candidate.,  64  (4.0): [PMID:33570950] [10.1021/acs.jmedchem.0c01863]

Source

Source(1):

• Scientific Literature