(Z)-1-(4-chlorophenyl)-3-(3-hydroxyphenylamino)but-2-en-1-one

ID: ALA1240890

Cas Number: 944153-47-3

PubChem CID: 877863

Max Phase: Preclinical

Molecular Formula: C16H14ClNO2

Molecular Weight: 287.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C/C(=O)c1ccc(Cl)cc1)Nc1cccc(O)c1

Standard InChI:  InChI=1S/C16H14ClNO2/c1-11(18-14-3-2-4-15(19)10-14)9-16(20)12-5-7-13(17)8-6-12/h2-10,18-19H,1H3/b11-9-

Standard InChI Key:  SNEQASFEVWLKOJ-LUAWRHEFSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    8.7257    2.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3192    1.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7400    1.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5670    1.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9716    1.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5485    2.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4943    1.7343    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.7965    1.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2198    1.0718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1981    2.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0230    2.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4246    3.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4463    1.8049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2712    1.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6906    1.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5148    1.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9172    1.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4894    2.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6667    2.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8885    3.2756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8 10  1  0
  2  3  1  0
 10 11  2  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 11 13  1  0
  1  2  2  0
 13 14  1  0
  2  7  1  0
 14 15  2  0
  3  4  2  0
 15 16  1  0
  5  8  1  0
 16 17  2  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
 19 14  1  0
  4  5  1  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1240890

   (Z)-1-(4-Chlorophenyl)-3-(3-hydroxyphenylamino)but-2-en-1-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 287.75

Molecular Weight (Monoisotopic): 287.0713

AlogP: 4.24

#Rotatable Bonds: 4

Polar Surface Area: 49.33

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.31

CX Basic pKa: ┄

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.65

Np Likeness Score: -0.73

References

1. Sarkar S, Perlstein EO, Imarisio S, Pineau S, Cordenier A, Maglathlin RL, Webster JA, Lewis TA, O'Kane CJ, Schreiber SL, Rubinsztein DC..  (2007)  Small molecules enhance autophagy and reduce toxicity in Huntington's disease models.,  3  (6): [PMID:17486044] [10.1038/nchembio883]

2. Ahamad S, Bhat SA..  (2022)  The Emerging Landscape of Small-Molecule Therapeutics for the Treatment of Huntington's Disease.,  65  (24.0): [PMID:36490325] [10.1021/acs.jmedchem.2c00799]

Source

Source(1):

• Scientific Literature