(E)-3-(3-tert-butyl-4-hydroxy-5-((E)-(thiazol-2-ylimino)methyl)phenyl)-1-(4-methoxyphenyl)prop-2-en-1-one

ID: ALA3260656

PubChem CID: 136498899

Max Phase: Preclinical

Molecular Formula: C24H24N2O3S

Molecular Weight: 420.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)/C=C/c2cc(/C=N/c3nccs3)c(O)c(C(C)(C)C)c2)cc1

Standard InChI:  InChI=1S/C24H24N2O3S/c1-24(2,3)20-14-16(5-10-21(27)17-6-8-19(29-4)9-7-17)13-18(22(20)28)15-26-23-25-11-12-30-23/h5-15,28H,1-4H3/b10-5+,26-15+

Standard InChI Key:  UEDWYGVLUBPSPP-IGWQBUHKSA-N

Molfile:  

     RDKit          2D

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   10.3444  -21.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0524  -22.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7621  -21.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7593  -20.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0507  -20.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0482  -19.7609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4654  -20.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1747  -20.9780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8808  -20.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6261  -20.8992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1706  -20.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7593  -19.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9607  -19.7567    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0522  -23.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7599  -23.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7597  -24.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4673  -24.6673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0518  -24.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3466  -24.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6392  -24.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6386  -25.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3512  -25.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0556  -25.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9313  -25.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6377  -20.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2232  -25.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9301  -20.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6375  -19.7613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9272  -20.1698    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
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 12 13  2  0
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 14 10  1  0
  3 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
  1 26  1  0
 25 27  1  0
 26 28  1  0
 26 29  1  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3260656

   ---

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: 420.53

Molecular Weight (Monoisotopic): 420.1508

AlogP: 5.80

#Rotatable Bonds: 6

Polar Surface Area: 71.78

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.95

CX Basic pKa: 0.28

CX LogP: 6.19

CX LogD: 6.18

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.31

Np Likeness Score: -0.67

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