(E)-1-(furan-2-yl)-3-(4-hydroxy-3-isopropyl-5-((E)-(thiazol-2-ylimino)methyl)phenyl)prop-2-en-1-one

ID: ALA3260651

PubChem CID: 136498894

Max Phase: Preclinical

Molecular Formula: C20H18N2O3S

Molecular Weight: 366.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1cc(/C=C/C(=O)c2ccco2)cc(/C=N/c2nccs2)c1O

Standard InChI:  InChI=1S/C20H18N2O3S/c1-13(2)16-11-14(5-6-17(23)18-4-3-8-25-18)10-15(19(16)24)12-22-20-21-7-9-26-20/h3-13,24H,1-2H3/b6-5+,22-12+

Standard InChI Key:  KQJBGKSAXADAFB-RIYRHGMWSA-N

Molfile:  

     RDKit          2D

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    8.7566  -10.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7554  -11.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4635  -11.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1731  -11.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1703  -10.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4617   -9.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4592   -9.0755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8765   -9.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5857  -10.2926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2919   -9.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0371  -10.2138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5816   -9.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1704   -8.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3717   -9.0713    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4633  -12.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1709  -12.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1707  -13.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8783  -13.9819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0488   -9.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4629  -13.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7144  -13.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1674  -14.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5759  -14.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3752  -14.7965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3411  -10.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0486   -9.0759    0.0000 C   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
  6  7  1  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
  3 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  1 19  1  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
 19 25  1  0
 19 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3260651

   ---

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: 366.44

Molecular Weight (Monoisotopic): 366.1038

AlogP: 5.21

#Rotatable Bonds: 6

Polar Surface Area: 75.69

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.80

CX Basic pKa: 0.28

CX LogP: 5.11

CX LogD: 5.09

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.37

Np Likeness Score: -0.80

References

1. Sashidhara KV, Rao KB, Kushwaha V, Modukuri RK, Verma R, Murthy PK..  (2014)  Synthesis and antifilarial activity of chalcone-thiazole derivatives against a human lymphatic filarial parasite, Brugia malayi.,  81  [PMID:24863844] [10.1016/j.ejmech.2014.05.029]

Source

Source(1):

• Scientific Literature