4-(5-chloro-2-hydroxy-3-methoxybenzylidene)-1-(3-chloro-4-fluorophenyl)pyrazolidine-3,5-dione

ID: ALA1668290

PubChem CID: 1220388

Max Phase: Preclinical

Molecular Formula: C17H11Cl2FN2O4

Molecular Weight: 397.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Cl)cc(/C=C2\C(=O)NN(c3ccc(F)c(Cl)c3)C2=O)c1O

Standard InChI:  InChI=1S/C17H11Cl2FN2O4/c1-26-14-6-9(18)4-8(15(14)23)5-11-16(24)21-22(17(11)25)10-2-3-13(20)12(19)7-10/h2-7,23H,1H3,(H,21,24)/b11-5+

Standard InChI Key:  GWJIIYQQCOQSJU-VZUCSPMQSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    9.2146    1.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2135    0.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9283    0.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6446    0.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6419    1.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9265    1.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3598    0.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0311    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9240    2.7501    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.8141    0.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3044    1.1557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8248    1.8270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0383    1.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3749    2.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0626   -0.2945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1292    1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5329    0.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3571    0.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7760    1.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3649    1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5420    1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9281   -0.5527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4988    0.2732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7846    0.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7805    2.5667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.6010    1.1285    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13  8  1  0
  1  2  2  0
 13 14  2  0
  4  7  1  0
 10 15  2  0
  3  4  2  0
 11 16  1  0
  7  8  2  0
 16 17  2  0
 17 18  1  0
  6  9  1  0
 18 19  2  0
  8 10  1  0
 19 20  1  0
  4  5  1  0
 20 21  2  0
 21 16  1  0
  2  3  1  0
  3 22  1  0
  5  6  2  0
  2 23  1  0
  6  1  1  0
 23 24  1  0
 10 11  1  0
 20 25  1  0
 11 12  1  0
 19 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1668290

   4-(5-Chloro-2-hydroxy-3-methoxybenzylidene)-1-(3-chloro-4-fluorophenyl)pyrazolidine-3,5-dione

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: 397.19

Molecular Weight (Monoisotopic): 396.0080

AlogP: 3.31

#Rotatable Bonds: 3

Polar Surface Area: 78.87

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.17

CX Basic pKa: ┄

CX LogP: 3.32

CX LogD: 2.53

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: -1.62

References

1. Chu Y, Chen X, Yang Y, Tang Y..  (2011)  Identification of small molecular inhibitors for Ero1p by structure-based virtual screening.,  21  (4): [PMID:21269829] [10.1016/j.bmcl.2010.12.129]

Source

Source(1):

• Scientific Literature