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

ID: ALA4576297

PubChem CID: 155552038

Max Phase: Preclinical

Molecular Formula: C23H29ClN4O2

Molecular Weight: 428.96

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCn1c(C)c2c(c1C)C(=O)N(CN1CCN(c3ccccc3Cl)CC1)C2=O

Standard InChI:  InChI=1S/C23H29ClN4O2/c1-4-5-10-27-16(2)20-21(17(27)3)23(30)28(22(20)29)15-25-11-13-26(14-12-25)19-9-7-6-8-18(19)24/h6-9H,4-5,10-15H2,1-3H3

Standard InChI Key:  YNDJJNHPVFHAAJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   23.5821  -19.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0806  -19.9198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3611  -19.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3350  -20.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1112  -20.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6172  -19.9976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1536  -19.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4332  -18.5391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3411  -21.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2643  -21.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3492  -18.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4418  -20.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8313  -20.7509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3898  -21.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7760  -22.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6008  -22.2073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0379  -21.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6502  -20.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2560  -19.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8644  -19.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0397  -19.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6482  -18.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9872  -22.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5479  -23.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9341  -24.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7594  -24.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1970  -23.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8083  -22.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2440  -22.2586    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0
  4  2  2  0
  2  3  1  0
  3  1  1  0
  4  5  1  0
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  1 11  1  0
  2 12  1  0
  7 13  1  0
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 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  3 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 17 24  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4576297

   ---

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: 428.96

Molecular Weight (Monoisotopic): 428.1979

AlogP: 3.93

#Rotatable Bonds: 6

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: 4.89

CX LogP: 4.41

CX LogD: 4.41

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -1.43

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