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

ID: ALA2286508

PubChem CID: 76316398

Max Phase: Preclinical

Molecular Formula: C15H15NO5

Molecular Weight: 289.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)CC2NC(=O)/C(=C(/C)O)C2=O)cc1

Standard InChI:  InChI=1S/C15H15NO5/c1-8(17)13-14(19)11(16-15(13)20)7-12(18)9-3-5-10(21-2)6-4-9/h3-6,11,17H,7H2,1-2H3,(H,16,20)/b13-8-

Standard InChI Key:  ZPKNQVASTCLEHY-JYRVWZFOSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    4.9733   -8.7002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7946   -8.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490   -7.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3819   -7.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7190   -7.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3806   -6.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2742   -9.3660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8306   -7.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4413   -8.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0017   -6.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376   -7.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3305   -8.2143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5491   -7.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5008   -9.0177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3798   -7.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5992   -6.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9912   -7.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650   -8.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9454   -8.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2095   -7.2012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0382   -6.3980    0.0000 C   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  1  0
 12 14  2  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 13  1  0
 17 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2286508

   4-Acetyl-3-hydroxy-2-[2-(4-methoxyphenyl)-2-oxoethyl]-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: 289.29

Molecular Weight (Monoisotopic): 289.0950

AlogP: 1.17

#Rotatable Bonds: 4

Polar Surface Area: 92.70

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.82

CX Basic pKa: ┄

CX LogP: 0.57

CX LogD: -1.96

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.38

Np Likeness Score: 0.53

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