1,3-Diethyl-5-(4-nitro-thiophen-2-ylmethylene)-2-thioxo-dihydro-pyrimidine-4,6-dione

ID: ALA356906

PubChem CID: 44367094

Max Phase: Preclinical

Molecular Formula: C13H13N3O4S2

Molecular Weight: 339.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1C(=O)C(=Cc2cc([N+](=O)[O-])cs2)C(=O)N(CC)C1=S

Standard InChI:  InChI=1S/C13H13N3O4S2/c1-3-14-11(17)10(12(18)15(4-2)13(14)21)6-9-5-8(7-22-9)16(19)20/h5-7H,3-4H2,1-2H3

Standard InChI Key:  YJDMUGIBFYFCQF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    9.5500    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1375    0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250    1.1958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8625   -0.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8250    1.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5667    0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8875    0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2417   -0.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0792    0.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2542    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9792    1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2792    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7167    1.6000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.4292   -0.0542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.7750   -1.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8125    2.4458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2917    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0667   -0.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4125    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8292   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5292   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6875    1.2333    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  9  1  0
  8  7  1  0
  9 11  2  0
 10  1  2  0
 11 10  1  0
 12 13  1  0
 13 11  1  0
 14  2  2  0
 15  8  1  0
 16  5  2  0
 17  6  2  0
 18  8  2  0
 19  3  1  0
 20  4  1  0
 21 20  1  0
 22 19  1  0
  2  3  1  0
 12  7  2  0
M  CHG  2   8   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA356906

   1,3-Diethyl-5-[(4-nitrothiophen-2-yl)methylidene]-2-sulfanylidene-1,3-diazinane-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: 339.40

Molecular Weight (Monoisotopic): 339.0347

AlogP: 2.04

#Rotatable Bonds: 4

Polar Surface Area: 83.76

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.69

CX LogD: 2.69

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.28

Np Likeness Score: -1.57

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