5-(2,3-dihydroxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione

ID: ALA5287271

Max Phase: Preclinical

Molecular Formula: C13H12N2O5

Molecular Weight: 276.25

Names and Identifiers

Canonical SMILES:  CN1C(=O)C(=Cc2cccc(O)c2O)C(=O)N(C)C1=O

Standard InChI:  InChI=1S/C13H12N2O5/c1-14-11(18)8(12(19)15(2)13(14)20)6-7-4-3-5-9(16)10(7)17/h3-6,16-17H,1-2H3

Standard InChI Key:  KBWSPGNYBUVVOM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    0.3587   -0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733   -0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851   -0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851   -1.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0751   -2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3587   -1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705    1.6497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3558    2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3587    1.6498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3587    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851    2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733    2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3558    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851    0.4120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733    0.4120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0751   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559   -2.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  1  7  1  0
  7  8  2  0
  9  8  1  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
  8 13  1  0
 10 14  1  0
 12 15  1  0
 11 16  2  0
  9 17  2  0
 13 18  2  0
  5 19  1  0
  6 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287271

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

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: 0.53

#Rotatable Bonds: 1

Polar Surface Area: 98.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.07

CX Basic pKa: ┄

CX LogP: 0.62

CX LogD: 0.61

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.44

Np Likeness Score: -0.51

References

1. Shi YY, Wei B, Zhou J, Yin ZL, Zhao F, Peng YJ, Yu QW, Wang XL, Chen YJ..  (2022)  Discovery of 5-(3,4-dihydroxybenzylidene)-1,3-dimethylpyrimidine- 2,4,6(1H,3H,5H)-trione as a novel and effective cardioprotective agent via dual anti-inflammatory and anti-oxidative activities.,  244  [PMID:36274277] [10.1016/j.ejmech.2022.114848]

Source

Source(1):

• Scientific Literature