(E)-3,5-Bis(4-pentafluorothiobenzylidene)-tetrahydrothiopyran-4-one

ID: ALA4091786

PubChem CID: 137652961

Max Phase: Preclinical

Molecular Formula: C19H14F10OS3

Molecular Weight: 544.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccc(S(F)(F)(F)(F)F)cc2)CSC/C1=C\c1ccc(S(F)(F)(F)(F)F)cc1

Standard InChI:  InChI=1S/C19H14F10OS3/c20-32(21,22,23,24)17-5-1-13(2-6-17)9-15-11-31-12-16(19(15)30)10-14-3-7-18(8-4-14)33(25,26,27,28)29/h1-10H,11-12H2/b15-9+,16-10+

Standard InChI Key:  VPIODVANGKMJSC-KAVGSWPWSA-N

Molfile:  

     RDKit          2D

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   36.1834   -2.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1834   -2.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8887   -3.3802    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.5940   -2.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5940   -2.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8887   -1.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3029   -1.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0094   -2.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8887   -0.9286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4745   -1.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7680   -2.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0597   -1.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3536   -2.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3556   -2.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0695   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7726   -2.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0054   -2.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7111   -3.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4210   -2.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4207   -2.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7145   -1.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6496   -3.3927    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.9402   -2.9871    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.6531   -4.2099    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.9365   -3.7971    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.6423   -2.5754    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.2242   -3.9704    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   41.1280   -3.3947    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   41.1267   -4.2119    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   41.8364   -2.9872    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   41.8336   -3.8012    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   41.1237   -2.5754    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   40.5459   -3.9704    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  6  9  2  0
  1 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  8 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  8  1  0
 14 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 22 26  1  0
 22 27  1  0
 19 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 28 32  1  0
 28 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091786

   ---

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: 544.50

Molecular Weight (Monoisotopic): 544.0047

AlogP: 9.78

#Rotatable Bonds: 4

Polar Surface Area: 17.07

Molecular Species: ┄

HBA: 2

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 9.25

CX LogD: 9.25

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.28

Np Likeness Score: -0.20

References

1. Schmitt F, Gold M, Begemann G, Andronache I, Biersack B, Schobert R..  (2017)  Fluoro and pentafluorothio analogs of the antitumoral curcuminoid EF24 with superior antiangiogenic and vascular-disruptive effects.,  25  (17): [PMID:28774574] [10.1016/j.bmc.2017.07.039]

Source

Source(1):

• Scientific Literature