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

ID: ALA4084209

PubChem CID: 91669153

Max Phase: Preclinical

Molecular Formula: C18H21N3O5S2

Molecular Weight: 423.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCN(S(=O)(=O)c2ccc(NC(=O)c3ccc([N+](=O)[O-])s3)cc2)CC1

Standard InChI:  InChI=1S/C18H21N3O5S2/c1-18(2)9-11-20(12-10-18)28(25,26)14-5-3-13(4-6-14)19-17(22)15-7-8-16(27-15)21(23)24/h3-8H,9-12H2,1-2H3,(H,19,22)

Standard InChI Key:  FQCDZESESIXPHE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    2.4373   -9.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8540   -9.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287   -9.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5831   -7.3037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997   -8.0203    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4120   -7.3011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7148   -8.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7137   -9.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4284   -9.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1449   -9.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1420   -8.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4267   -8.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2855   -8.4332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5727   -8.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8606   -8.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5712   -9.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2895   -9.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8600   -9.6709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2888   -9.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5724   -8.4324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3790  -10.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1862  -10.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5975   -9.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0445   -9.3296    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4178   -9.8541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9038  -10.5207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7522   -9.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  2  0
  6  5  2  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  7  5  1  0
  5 13  1  0
 13 14  1  0
 13 17  1  0
 14 15  1  0
 15  2  1  0
  2 16  1  0
 16 17  1  0
 10 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:

   

   ALA4084209

   N-[4-(4,4-dimethylpiperidin-1-yl)sulfonylphenyl]-5-nitrothiophene-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: 423.52

Molecular Weight (Monoisotopic): 423.0923

AlogP: 3.72

#Rotatable Bonds: 5

Polar Surface Area: 109.62

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.51

CX Basic pKa: ┄

CX LogP: 3.57

CX LogD: 3.57

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -1.99

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