4,6-dimethyl-5-(3-chlorophenyl)-2{[4-(o-fluorophenyl)-1-piperazinyl]methyl}pyrrolo[3,4-c]pyrrole-1,3(2H,5H)-dione

ID: ALA4559732

PubChem CID: 155558071

Max Phase: Preclinical

Molecular Formula: C25H24ClFN4O2

Molecular Weight: 466.94

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c2c(c(C)n1-c1cccc(Cl)c1)C(=O)N(CN1CCN(c3ccccc3F)CC1)C2=O

Standard InChI:  InChI=1S/C25H24ClFN4O2/c1-16-22-23(17(2)31(16)19-7-5-6-18(26)14-19)25(33)30(24(22)32)15-28-10-12-29(13-11-28)21-9-4-3-8-20(21)27/h3-9,14H,10-13,15H2,1-2H3

Standard InChI Key:  KBRVEXFINIFEFA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   22.6535   -3.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1520   -3.7665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4325   -3.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4063   -4.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.6885   -3.8442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2249   -3.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5046   -2.3856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4124   -5.2883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3357   -5.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4205   -2.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5131   -3.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9028   -4.5976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4612   -5.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.6721   -6.0540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1093   -5.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.0586   -6.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6192   -7.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0055   -8.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8308   -8.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2684   -7.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8797   -6.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3153   -6.1052    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.3279   -3.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9369   -3.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1130   -2.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6791   -3.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0751   -4.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8977   -4.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7217   -2.2652    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0
  4  2  2  0
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  8  9  2  0
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 27 28  2  0
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 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
  3 27  1  0
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4559732

   ---

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: 466.94

Molecular Weight (Monoisotopic): 466.1572

AlogP: 4.26

#Rotatable Bonds: 4

Polar Surface Area: 48.79

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.02

CX LogP: 4.89

CX LogD: 4.89

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.54

Np Likeness Score: -1.73

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