4-(Isoquinolin-5-ylsulfonyl)-N-(4-methyl-2-nitrophenyl)piperazine-1-carboxamide

ID: ALA4514482

PubChem CID: 155539329

Max Phase: Preclinical

Molecular Formula: C21H21N5O5S

Molecular Weight: 455.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)N2CCN(S(=O)(=O)c3cccc4cnccc34)CC2)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C21H21N5O5S/c1-15-5-6-18(19(13-15)26(28)29)23-21(27)24-9-11-25(12-10-24)32(30,31)20-4-2-3-16-14-22-8-7-17(16)20/h2-8,13-14H,9-12H2,1H3,(H,23,27)

Standard InChI Key:  CIRUPWKJVQXNRA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   29.1289  -27.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9538  -27.7955    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.5414  -27.0810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8232  -29.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8221  -29.8687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5369  -30.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5351  -28.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2504  -29.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2512  -29.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9665  -30.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6815  -29.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6768  -29.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9609  -28.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6688  -27.3823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3807  -27.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0909  -27.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0908  -26.5555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3742  -26.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6578  -26.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8045  -26.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5197  -26.5533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8033  -25.3169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.2335  -26.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9496  -26.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6613  -26.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6644  -25.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9494  -24.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2314  -25.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3797  -24.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9486  -27.3797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2336  -27.7913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6625  -27.7931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 13  2  1  0
  2 14  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 23 24  1  0
 23 28  2  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 26 29  1  0
 24 30  1  0
 30 31  1  0
 30 32  2  0
M  CHG  2  30   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4514482

   ---

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: 455.50

Molecular Weight (Monoisotopic): 455.1263

AlogP: 2.99

#Rotatable Bonds: 4

Polar Surface Area: 125.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.78

CX Basic pKa: 3.42

CX LogP: 2.23

CX LogD: 2.23

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.48

Np Likeness Score: -2.17

References

1. Singh V, Pacitto A, Donini S, Ferraris DM, Boros S, Illyés E, Szokol B, Rizzi M, Blundell TL, Ascher DB, Pato J, Mizrahi V..  (2019)  Synthesis and Structure-Activity relationship of 1-(5-isoquinolinesulfonyl)piperazine analogues as inhibitors of Mycobacterium tuberculosis IMPDH.,  174  [PMID:31055147] [10.1016/j.ejmech.2019.04.027]

Source

Source(1):

• Scientific Literature