5-(2-chlorobenzyl)-3-(1-hydroxyethylidene)pyrrolidine-2,4-dione

ID: ALA2286514

PubChem CID: 76320090

Max Phase: Preclinical

Molecular Formula: C13H12ClNO3

Molecular Weight: 265.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(O)=C1/C(=O)NC(Cc2ccccc2Cl)C1=O

Standard InChI:  InChI=1S/C13H12ClNO3/c1-7(16)11-12(17)10(15-13(11)18)6-8-4-2-3-5-9(8)14/h2-5,10,16H,6H2,1H3,(H,15,18)/b11-7-

Standard InChI Key:  PIZAXQOUIHTKTG-XFFZJAGNSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   12.9471   -3.6320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7684   -3.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0228   -2.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3598   -2.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6969   -2.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3586   -1.5436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2521   -4.2978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8044   -2.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4151   -3.1474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9796   -1.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9155   -2.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3043   -3.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5237   -2.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9129   -3.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0870   -4.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8733   -4.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4767   -3.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3549   -2.0877    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  4  6  2  0
  2  7  2  0
  3  8  2  0
  8  9  1  0
  8 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 13 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2286514

   4-Acetyl-2-[(2-chlorophenyl)methyl]-3-hydroxy-1,2-dihydropyrrol-5-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: 265.70

Molecular Weight (Monoisotopic): 265.0506

AlogP: 1.78

#Rotatable Bonds: 2

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.73

CX Basic pKa: ┄

CX LogP: 1.88

CX LogD: -0.73

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.49

Np Likeness Score: 0.23

References

1. Han BF, Shi QM, Wang XF, Liu JB, Qiang S, Yang CL.  (2012)  Synthesis and bioactivity of novel 3-(1-hydroxyethylidene)-5-substituted-pyrrolidine-2,4-dione derivatives,  23  (9): [10.1016/j.cclet.2012.07.002]

Source

Source(1):

• Scientific Literature