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

ID: ALA357999

PubChem CID: 135921198

Max Phase: Preclinical

Molecular Formula: C17H16N4O4S

Molecular Weight: 372.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1C(=O)C(=Cc2c[nH]c3ccc([N+](=O)[O-])cc23)C(=O)N(CC)C1=S

Standard InChI:  InChI=1S/C17H16N4O4S/c1-3-19-15(22)13(16(23)20(4-2)17(19)26)7-10-9-18-14-6-5-11(21(24)25)8-12(10)14/h5-9,18H,3-4H2,1-2H3

Standard InChI Key:  KYORFUQOULAHND-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   10.0167   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6042   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5917   -1.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3292   -2.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2917   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375   -2.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7167   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4417   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4542    0.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1875   -1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3542   -2.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5417   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2167   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4167   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9000   -2.9917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7500   -1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2542    0.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2792   -0.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7625   -2.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8875    1.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7917   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2917   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8792   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5500   -1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9917   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1542   -1.7042    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  1  2  0
  8  7  1  0
  9 13  1  0
 10  8  1  0
 11 12  1  0
 12  8  2  0
 13 14  2  0
 14 10  1  0
 15  2  2  0
 16 10  2  0
 17  9  1  0
 18  5  2  0
 19  6  2  0
 20  9  2  0
 21 24  2  0
 22  4  1  0
 23  3  1  0
 24 16  1  0
 25 22  1  0
 26 23  1  0
  2  3  1  0
 16 11  1  0
 21 13  1  0
M  CHG  2   9   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA357999

   ---

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: 372.41

Molecular Weight (Monoisotopic): 372.0892

AlogP: 2.46

#Rotatable Bonds: 4

Polar Surface Area: 99.55

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: 2.87

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.29

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