N-(3-(4,4-dimethylpiperidin-1-ylsulfonyl)phenyl)-5-nitrofuran-2-carboxamide

ID: ALA4099712

PubChem CID: 86289018

Max Phase: Preclinical

Molecular Formula: C18H21N3O6S

Molecular Weight: 407.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCN(S(=O)(=O)c2cccc(NC(=O)c3ccc([N+](=O)[O-])o3)c2)CC1

Standard InChI:  InChI=1S/C18H21N3O6S/c1-18(2)8-10-20(11-9-18)28(25,26)14-5-3-4-13(12-14)19-17(22)15-6-7-16(27-15)21(23)24/h3-7,12H,8-11H2,1-2H3,(H,19,22)

Standard InChI Key:  FVTVAONYIKUKFQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    7.5955   -9.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0101   -8.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1888   -8.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6022   -7.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5830   -6.6289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1688   -7.3514    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4513   -7.7662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7352   -7.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3237   -8.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8860   -8.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8871   -7.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0199   -7.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7502   -6.6316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3208   -7.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6040   -9.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7338   -9.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4553   -8.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0302   -7.3490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7427   -7.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4521   -7.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7458   -8.5777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2005   -7.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7475   -7.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3343   -6.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5321   -6.5245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6653   -5.5995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4814   -5.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1803   -4.9372    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 20  1  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4099712

   N-[3-(4,4-dimethylpiperidin-1-yl)sulfonylphenyl]-5-nitrofuran-2-carboxamide

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: 407.45

Molecular Weight (Monoisotopic): 407.1151

AlogP: 3.25

#Rotatable Bonds: 5

Polar Surface Area: 122.76

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.95

CX Basic pKa: ┄

CX LogP: 2.65

CX LogD: 2.65

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: -1.97

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