N-(4-(3-azaspiro[5.5]undecan-3-ylsulfonyl)phenyl)-5-nitrothiophene-2-carboxamide

ID: ALA4091964

PubChem CID: 91669152

Max Phase: Preclinical

Molecular Formula: C21H25N3O5S2

Molecular Weight: 463.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(S(=O)(=O)N2CCC3(CCCCC3)CC2)cc1)c1ccc([N+](=O)[O-])s1

Standard InChI:  InChI=1S/C21H25N3O5S2/c25-20(18-8-9-19(30-18)24(26)27)22-16-4-6-17(7-5-16)31(28,29)23-14-12-21(13-15-23)10-2-1-3-11-21/h4-9H,1-3,10-15H2,(H,22,25)

Standard InChI Key:  ORDYTITZWUSMJW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    3.8456   -9.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289   -8.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174   -9.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162  -10.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1329  -10.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8506  -10.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5746   -7.2412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9913   -7.9578    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4036   -7.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7065   -8.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7053   -9.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4201   -9.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1365   -9.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1337   -8.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4182   -7.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771   -8.3707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5642   -7.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8522   -8.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -9.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2812   -9.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8515   -9.6084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5653   -9.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2804   -9.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5640   -8.3699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3706  -10.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1778  -10.5943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5892   -9.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0362   -9.2671    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.4095   -9.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8954  -10.4582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7437   -9.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  8  7  2  0
  9  8  2  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 10  8  1  0
  8 16  1  0
 16 17  1  0
 16 20  1  0
 17 18  1  0
 18  1  1  0
  1 19  1  0
 19 20  1  0
 13 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 23  1  0
 27 29  1  0
 29 30  2  0
 29 31  1  0
M  CHG  2  29   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4091964

   N-[4-(3-azaspiro[5.5]undecan-3-ylsulfonyl)phenyl]-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: 463.58

Molecular Weight (Monoisotopic): 463.1236

AlogP: 4.64

#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: 4.44

CX LogD: 4.44

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.51

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