N-(3-(4,4-dimethylpiperidin-1-ylsulfonyl)phenyl)-3-nitrobenzamide

ID: ALA4061428

PubChem CID: 86289020

Max Phase: Preclinical

Molecular Formula: C20H23N3O5S

Molecular Weight: 417.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCN(S(=O)(=O)c2cccc(NC(=O)c3cccc([N+](=O)[O-])c3)c2)CC1

Standard InChI:  InChI=1S/C20H23N3O5S/c1-20(2)9-11-22(12-10-20)29(27,28)18-8-4-6-16(14-18)21-19(24)15-5-3-7-17(13-15)23(25)26/h3-8,13-14H,9-12H2,1-2H3,(H,21,24)

Standard InChI Key:  CPNPLVKGJLWYBV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    6.0117   -9.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4263   -8.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6050   -8.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0184   -7.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9992   -6.6580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5850   -7.3804    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8676   -7.7952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1514   -7.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7400   -8.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3023   -8.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3034   -7.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4362   -7.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1664   -6.6606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7371   -7.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0202   -9.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1500   -9.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8716   -8.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4465   -7.3780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1589   -7.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8683   -7.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1620   -8.6067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5798   -7.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2887   -7.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2861   -6.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5687   -6.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8627   -6.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0011   -7.7777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0037   -8.5987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7106   -7.3650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  2 16  1  0
  7  8  1  0
  6 13  2  0
 15  9  2  0
  6  7  1  0
  4 11  1  0
  7 17  1  0
 11  6  1  0
 11 10  2  0
 10 15  1  0
  9 14  1  0
 16 17  1  0
  8 12  1  0
  5  6  2  0
 12  2  1  0
 14  4  2  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 20  1  0
 23 27  1  0
 27 28  1  0
 27 29  2  0
M  CHG  2  27   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4061428

   N-[3-(4,4-dimethylpiperidin-1-yl)sulfonylphenyl]-3-nitrobenzamide

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: 417.49

Molecular Weight (Monoisotopic): 417.1358

AlogP: 3.66

#Rotatable Bonds: 5

Polar Surface Area: 109.62

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.36

CX Basic pKa: ┄

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.59

Np Likeness Score: -1.86

References

1. Hackler A, Patrick SL, Kahney EW, Flaherty DP, Sharlow ER, Morris JC, Golden JE..  (2017)  Antiparasitic lethality of sulfonamidebenzamides in kinetoplastids.,  27  (4): [PMID:28119024] [10.1016/j.bmcl.2017.01.043]

Source

Source(1):

• Scientific Literature