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

ID: ALA3260657

PubChem CID: 136498900

Max Phase: Preclinical

Molecular Formula: C21H20N2O3S

Molecular Weight: 380.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H20N2O3S/c1-21(2,3)16-12-14(6-7-17(24)18-5-4-9-26-18)11-15(19(16)25)13-23-20-22-8-10-27-20/h4-13,25H,1-3H3/b7-6+,23-13+

Standard InChI Key:  LGEYRXCDYFAJIX-IFYJTALQSA-N

Molfile:  

     RDKit          2D

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   17.8931  -22.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6011  -23.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3108  -22.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3080  -21.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5994  -21.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5969  -20.7060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0141  -21.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7234  -21.9231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4295  -21.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1748  -21.8444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7193  -21.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3080  -20.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5094  -20.7018    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.6009  -23.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3086  -24.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3084  -25.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0160  -25.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1864  -21.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6005  -25.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8521  -25.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3051  -25.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7135  -26.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5129  -26.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4788  -21.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1862  -20.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4759  -21.1149    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
 19 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3260657

   ---

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: 380.47

Molecular Weight (Monoisotopic): 380.1195

AlogP: 5.39

#Rotatable Bonds: 5

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: 8.94

CX Basic pKa: 0.28

CX LogP: 5.41

CX LogD: 5.40

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.37

Np Likeness Score: -0.93

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