3-Ethyl-5-[1-[5-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl)-thiophen-2-yl]-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one

ID: ALA357092

PubChem CID: 44367072

Max Phase: Preclinical

Molecular Formula: C15H12F3N3OS3

Molecular Weight: 403.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1C(=O)/C(=C/c2ccc(-c3cc(C(F)(F)F)nn3C)s2)SC1=S

Standard InChI:  InChI=1S/C15H12F3N3OS3/c1-3-21-13(22)11(25-14(21)23)6-8-4-5-10(24-8)9-7-12(15(16,17)18)19-20(9)2/h4-7H,3H2,1-2H3/b11-6-

Standard InChI Key:  KEBYCDOAKSSMIY-WDZFZDKYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -1.9458    1.3583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875    0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6250   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083    1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -2.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2750    1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3750   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -1.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625    0.5708    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792    1.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000    0.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875    1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750   -0.0917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833    2.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -3.1000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -3.4625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -2.4667    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7250    1.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9000    2.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  3  1  1  0
  4 11  1  0
  5  7  1  0
  6  9  1  0
  7  1  1  0
  8  4  2  0
  9  4  1  0
 10  3  1  0
 11 14  1  0
 12  2  1  0
 13  5  2  0
 14 15  1  0
 15 13  1  0
 16 18  1  0
 17  3  2  0
 18 15  2  0
 19  7  2  0
 20 12  1  0
 21 12  1  0
 22 12  1  0
 23  1  1  0
 24  9  1  0
 25 23  1  0
  5 10  1  0
 16 11  2  0
  2  6  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA357092

   (5Z)-3-ethyl-5-[[5-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]thiophen-2-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one

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: 403.48

Molecular Weight (Monoisotopic): 403.0095

AlogP: 4.39

#Rotatable Bonds: 3

Polar Surface Area: 38.13

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.49

CX LogD: 4.49

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: -2.26

References

1. Voss ME, Carter PH, Tebben AJ, Scherle PA, Brown GD, Thompson LA, Xu M, Lo YC, Yang G, Liu RQ, Strzemienski P, Everlof JG, Trzaskos JM, Decicco CP..  (2003)  Both 5-arylidene-2-thioxodihydropyrimidine-4,6(1H,5H)-diones and 3-thioxo-2,3-dihydro-1H-imidazo[1,5-a]indol-1-ones are light-dependent tumor necrosis factor-alpha antagonists.,  13  (3): [PMID:12565966] [10.1016/s0960-894x(02)00941-1]

Source

Source(1):

• Scientific Literature