1-Ethyl-5-(3-naphthalen-1-yl-allylidene)-2-thioxo-dihydropyrimidine-4,6-dione

ID: ALA4175148

PubChem CID: 145952583

Max Phase: Preclinical

Molecular Formula: C19H16N2O2S

Molecular Weight: 336.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1C(=O)/C(=C/C=C/c2cccc3ccccc23)C(=O)NC1=S

Standard InChI:  InChI=1S/C19H16N2O2S/c1-2-21-18(23)16(17(22)20-19(21)24)12-6-10-14-9-5-8-13-7-3-4-11-15(13)14/h3-12H,2H2,1H3,(H,20,22,24)/b10-6+,16-12+

Standard InChI Key:  GLVPOCYTZXVYNM-RTTAIKLSSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   14.8094   -9.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1016   -9.6052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3938   -9.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3938   -8.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1016   -7.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8094   -8.3786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6819   -9.6052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1016   -7.1520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5213   -9.6052    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.6819   -7.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9741   -8.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2664   -7.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5586   -8.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5586   -9.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8467   -9.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1389   -9.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1389   -8.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4312   -7.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4312   -7.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1389   -6.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8467   -7.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8467   -7.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5213   -7.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2290   -8.3786    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  6  1  0
  1  6  1  0
  3  7  2  0
  5  8  2  0
  1  9  2  0
 10 11  1  0
 11 12  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 13 22  2  0
 17 22  1  0
 12 13  1  0
  4 10  2  0
 23 24  1  0
  6 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4175148

   ---

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: 336.42

Molecular Weight (Monoisotopic): 336.0932

AlogP: 3.04

#Rotatable Bonds: 3

Polar Surface Area: 49.41

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.70

CX Basic pKa: ┄

CX LogP: 3.77

CX LogD: 3.60

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.53

Np Likeness Score: -1.06

References

1. Ramisetti SR, Pandey MK, Lee SY, Karelia D, Narayan S, Amin S, Sharma AK..  (2018)  Design and synthesis of novel thiobarbituric acid derivatives targeting both wild-type and BRAF-mutated melanoma cells.,  143  [PMID:29133035] [10.1016/j.ejmech.2017.11.006]

Source

Source(1):

• Scientific Literature