4,6-dimethyl-5-phenyl-2-[(N-methylsulphonylpiperazinyl)methyl]pyrrolo[3,4-c]pyrrole-1,3(2H,5H)-dione

ID: ALA4475138

PubChem CID: 155537370

Max Phase: Preclinical

Molecular Formula: C20H24N4O4S

Molecular Weight: 416.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c2c(c(C)n1-c1ccccc1)C(=O)N(CN1CCN(S(C)(=O)=O)CC1)C2=O

Standard InChI:  InChI=1S/C20H24N4O4S/c1-14-17-18(15(2)24(14)16-7-5-4-6-8-16)20(26)23(19(17)25)13-21-9-11-22(12-10-21)29(3,27)28/h4-8H,9-13H2,1-3H3

Standard InChI Key:  KJOANMMLKQBFLO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   38.0903  -21.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.3779  -21.9926    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   38.0949  -22.4013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9353  -19.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9741  -18.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4727  -18.9804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7531  -18.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7270  -19.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5031  -19.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0090  -19.0582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5455  -18.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8251  -17.5997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7329  -20.5022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6564  -20.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7413  -17.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8335  -19.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2230  -19.8115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7815  -20.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1677  -21.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9924  -21.2676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4295  -20.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0419  -19.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6487  -18.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2577  -18.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4341  -18.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0002  -18.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3962  -19.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2187  -19.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9417  -22.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  8  2  0
  7  5  2  0
  5  6  1  0
  6  4  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
 11 12  2  0
  9 13  2  0
  4 14  1  0
  5 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
  6 23  1  0
 20  2  1  0
  2 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475138

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 416.50

Molecular Weight (Monoisotopic): 416.1518

AlogP: 1.22

#Rotatable Bonds: 4

Polar Surface Area: 82.93

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.92

CX LogP: 0.98

CX LogD: 0.98

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -1.51

References

1. Redzicka A, Szczukowski Ł, Kochel A, Wiatrak B, Gębczak K, Czyżnikowska Ż..  (2019)  COX-1/COX-2 inhibition activities and molecular docking study of newly designed and synthesized pyrrolo[3,4-c]pyrrole Mannich bases.,  27  (17): [PMID:31345747] [10.1016/j.bmc.2019.07.033]

Source

Source(1):

• Scientific Literature