N-(4-(2H-pyran-4-ylsulfonyl)phenyl)-5-nitrofuran-2-carboxamide

ID: ALA4072774

PubChem CID: 137640075

Max Phase: Preclinical

Molecular Formula: C16H12N2O7S

Molecular Weight: 376.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(S(=O)(=O)C2=CCOC=C2)cc1)c1ccc([N+](=O)[O-])o1

Standard InChI:  InChI=1S/C16H12N2O7S/c19-16(14-5-6-15(25-14)18(20)21)17-11-1-3-12(4-2-11)26(22,23)13-7-9-24-10-8-13/h1-9H,10H2,(H,17,19)

Standard InChI Key:  PNJKDVBMHODAEH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    4.6930   -8.0910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4212   -6.1463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8375   -6.8626    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2496   -6.1438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5524   -7.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5512   -8.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2656   -8.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9816   -8.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9787   -7.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2638   -6.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237   -7.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4113   -6.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6996   -7.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4099   -8.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1278   -8.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6963   -8.5123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4097   -8.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1244   -8.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4084   -7.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2070   -9.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0147   -9.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4252   -8.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8700   -8.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2449   -8.6954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7322   -9.3605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5772   -7.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  5  3  1  0
  3 11  1  0
 11 12  1  0
 11 15  2  0
 12 13  2  0
 13  1  1  0
  1 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 20 21  1  0
 18 20  2  0
 21 22  2  0
 22 23  1  0
 23 18  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4072774

   ---

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: 376.35

Molecular Weight (Monoisotopic): 376.0365

AlogP: 2.64

#Rotatable Bonds: 5

Polar Surface Area: 128.75

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.25

CX Basic pKa: ┄

CX LogP: 1.55

CX LogD: 1.55

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -1.30

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