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

ID: ALA2286515

PubChem CID: 76316401

Max Phase: Preclinical

Molecular Formula: C13H12N2O5

Molecular Weight: 276.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(O)=C1/C(=O)NC(Cc2ccc([N+](=O)[O-])cc2)C1=O

Standard InChI:  InChI=1S/C13H12N2O5/c1-7(16)11-12(17)10(14-13(11)18)6-8-2-4-9(5-3-8)15(19)20/h2-5,10,16H,6H2,1H3,(H,14,18)/b11-7-

Standard InChI Key:  BWJKBKKFCSBSQC-XFFZJAGNSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   20.9250   -3.6568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7422   -3.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9966   -2.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3336   -2.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6749   -2.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3324   -1.5807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2218   -4.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7741   -2.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3807   -3.1762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9451   -1.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8976   -2.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2905   -3.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5141   -2.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9073   -3.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0774   -4.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8595   -4.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4629   -3.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4686   -4.8158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6399   -5.6148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6910   -4.5646    0.0000 O   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
 18 19  2  0
 18 20  1  0
 15 18  1  0
M  CHG  2  18   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2286515

   4-Acetyl-3-hydroxy-2-[(4-nitrophenyl)methyl]-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: 276.25

Molecular Weight (Monoisotopic): 276.0746

AlogP: 1.04

#Rotatable Bonds: 3

Polar Surface Area: 109.54

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.68

CX Basic pKa: ┄

CX LogP: 1.21

CX LogD: -1.45

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.28

Np Likeness Score: 0.26

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