1,3-Diethyl-2-thioxo-5-[5-(2-trifluoromethyl-phenyl)-furan-2-ylmethylene]-dihydro-pyrimidine-4,6-dione

ID: ALA151153

PubChem CID: 44366867

Max Phase: Preclinical

Molecular Formula: C20H17F3N2O3S

Molecular Weight: 422.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1C(=O)C(=Cc2ccc(-c3ccccc3C(F)(F)F)o2)C(=O)N(CC)C1=S

Standard InChI:  InChI=1S/C20H17F3N2O3S/c1-3-24-17(26)14(18(27)25(4-2)19(24)29)11-12-9-10-16(28-12)13-7-5-6-8-15(13)20(21,22)23/h5-11H,3-4H2,1-2H3

Standard InChI Key:  UGIAZQPJKZTYIA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.3500   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292    0.4708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9625   -0.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3125    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542   -0.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9792   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7042    0.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5500   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2292   -0.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3167   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1542   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9375   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5375   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -0.5875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.1250    0.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4875    1.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3625   -1.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7417   -1.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417    1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1042   -1.2875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.4042   -1.9167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.5042   -0.9292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.1042   -3.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5375   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1542    1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3167   -2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7042   -3.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4917   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  1  1  0
  6  1  1  0
  7 10  1  0
  8  1  2  0
  9 13  1  0
 10 11  1  0
 11  8  1  0
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 14 16  1  0
 15  2  2  0
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 23  9  1  0
 24 13  2  0
 25 12  2  0
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 27 19  1  0
 28 25  1  0
 29 28  2  0
  2  3  1  0
 14  7  2  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA151153

   1,3-Diethyl-2-thioxo-5-[5-(2-trifluoromethyl-phenyl)-furan-2-ylmethylene]-dihydro-pyrimidine-4,6-dione

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: 422.43

Molecular Weight (Monoisotopic): 422.0912

AlogP: 4.34

#Rotatable Bonds: 4

Polar Surface Area: 53.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.34

CX LogD: 4.34

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: -1.29

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