4-(2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)acetamido)phenyl-4-(nitrooxy)butanoate

ID: ALA4289108

PubChem CID: 145989466

Max Phase: Preclinical

Molecular Formula: C19H17N3O9S

Molecular Weight: 463.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN1C(=O)c2ccccc2S1(=O)=O)Nc1ccc(OC(=O)CCCO[N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C19H17N3O9S/c23-17(12-21-19(25)15-4-1-2-5-16(15)32(21,28)29)20-13-7-9-14(10-8-13)31-18(24)6-3-11-30-22(26)27/h1-2,4-5,7-10H,3,6,11-12H2,(H,20,23)

Standard InChI Key:  KQEAMSGRPIHTFC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   34.9783   -1.6839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9824   -2.5011    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.6880   -2.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7935   -2.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7924   -3.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5004   -3.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4987   -2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2073   -2.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2075   -3.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9862   -3.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4672   -3.1664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2389   -4.6060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2844   -3.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6924   -2.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5096   -2.4569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.2832   -1.7503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9188   -3.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5076   -3.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9161   -4.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7342   -4.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1420   -3.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7311   -3.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1443   -5.2819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.9615   -5.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3717   -5.9869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.3686   -4.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1858   -4.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5928   -3.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4100   -3.8593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.8170   -3.1507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.6342   -3.1489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4069   -2.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  2  8  1  0
 10 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
M  CHG  2  30   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4289108

   ---

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: 463.42

Molecular Weight (Monoisotopic): 463.0686

AlogP: 1.36

#Rotatable Bonds: 9

Polar Surface Area: 162.22

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.82

CX Basic pKa: ┄

CX LogP: 1.60

CX LogD: 1.60

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.19

Np Likeness Score: -1.54

References

1. Das M, Bhattacharjee S, Fronczek FR, Bazan NG, Trudell ML..  (2018)  Synthesis, hepatotoxic evaluation and antipyretic activity of nitrate ester analogs of the acetaminophen derivative SCP-1.,  28  (23-24): [PMID:30327145] [10.1016/j.bmcl.2018.09.020]

Source

Source(1):

• Scientific Literature