(E)-1-(4-(3-fluorobenzyl)piperazin-1-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one

ID: ALA4873165

PubChem CID: 164624825

Max Phase: Preclinical

Molecular Formula: C21H23FN2O3

Molecular Weight: 370.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)N2CCN(Cc3cccc(F)c3)CC2)ccc1O

Standard InChI:  InChI=1S/C21H23FN2O3/c1-27-20-14-16(5-7-19(20)25)6-8-21(26)24-11-9-23(10-12-24)15-17-3-2-4-18(22)13-17/h2-8,13-14,25H,9-12,15H2,1H3/b8-6+

Standard InChI Key:  WCESATJMEGZLEK-SOFGYWHQSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   30.4204  -14.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4192  -15.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1273  -15.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8369  -15.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8341  -14.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1255  -13.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7126  -13.9914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7124  -13.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7112  -15.6274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5403  -13.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2495  -14.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9557  -13.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6649  -14.3856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.6657  -15.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3709  -15.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0794  -15.1994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0783  -14.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3686  -13.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9526  -13.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7871  -15.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4949  -15.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2001  -15.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9073  -15.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9077  -14.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1951  -13.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4907  -14.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6148  -15.6096    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  1  0
  2  9  1  0
  5 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 12 19  2  0
 16 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873165

   ---

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: 370.42

Molecular Weight (Monoisotopic): 370.1693

AlogP: 2.90

#Rotatable Bonds: 5

Polar Surface Area: 53.01

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.89

CX Basic pKa: 6.30

CX LogP: 3.03

CX LogD: 2.99

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -0.87

References

1. Singh YP, Shankar G, Jahan S, Singh G, Kumar N, Barik A, Upadhyay P, Singh L, Kamble K, Singh GK, Tiwari S, Garg P, Gupta S, Modi G..  (2021)  Further SAR studies on natural template based neuroprotective molecules for the treatment of Alzheimer's disease.,  46  [PMID:34481338] [10.1016/j.bmc.2021.116385]

Source

Source(1):

• Scientific Literature