2-(4-(((6-((3-Chlorobenzyl)thio)-4-oxo-4,5-dihydro-1,3,5-triazin-2-yl)thio)methyl)phenyl)propanoic acid

ID: ALA4528607

PubChem CID: 155544885

Max Phase: Preclinical

Molecular Formula: C20H18ClN3O3S2

Molecular Weight: 447.97

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C(=O)O)c1ccc(CSc2nc(SCc3cccc(Cl)c3)[nH]c(=O)n2)cc1

Standard InChI:  InChI=1S/C20H18ClN3O3S2/c1-12(17(25)26)15-7-5-13(6-8-15)10-28-19-22-18(27)23-20(24-19)29-11-14-3-2-4-16(21)9-14/h2-9,12H,10-11H2,1H3,(H,25,26)(H,22,23,24,27)

Standard InChI Key:  QMNBNKLGYMHKDS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   37.7173   -4.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7162   -5.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4242   -5.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1339   -5.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1311   -4.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4224   -4.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8372   -4.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8341   -3.2418    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   40.5403   -2.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2447   -3.2393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.9488   -2.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9499   -2.0140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.2408   -1.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5306   -2.0154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.6565   -3.2402    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   42.6564   -4.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2405   -0.7887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.3642   -4.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3620   -5.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0689   -5.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7776   -5.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7750   -4.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0675   -4.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4240   -6.5196    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   45.4858   -5.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4869   -6.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1930   -5.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.9012   -5.6896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.1919   -4.4648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 14  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  1  0
 13 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  3 24  1  0
 21 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4528607

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 447.97

Molecular Weight (Monoisotopic): 447.0478

AlogP: 4.59

#Rotatable Bonds: 8

Polar Surface Area: 95.94

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.97

CX Basic pKa: ┄

CX LogP: 5.59

CX LogD: 1.53

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -1.30

References

1. Bergant K, Janežič M, Valjavec K, Sosič I, Pajk S, Štampar M, Žegura B, Gobec S, Filipič M, Perdih A..  (2019)  Structure-guided optimization of 4,6-substituted-1,3,5-triazin-2(1H)-ones as catalytic inhibitors of human DNA topoisomerase IIα.,  175  [PMID:31096154] [10.1016/j.ejmech.2019.04.055]

Source

Source(1):

• Scientific Literature