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

ID: ALA4281901

PubChem CID: 145982218

Max Phase: Preclinical

Molecular Formula: C18H15N3O9S

Molecular Weight: 449.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H15N3O9S/c22-16(11-20-18(24)14-3-1-2-4-15(14)31(20,27)28)19-12-5-7-13(8-6-12)30-17(23)9-10-29-21(25)26/h1-8H,9-11H2,(H,19,22)

Standard InChI Key:  ARUZCDMXRQVPMH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   29.1740   -4.5834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9912   -4.5831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4000   -5.2907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3996   -3.8753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5594   -2.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5636   -3.2234    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.2692   -2.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3747   -3.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3736   -4.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0816   -4.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0798   -3.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7884   -3.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7887   -4.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5674   -4.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0484   -3.8886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8201   -5.3282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8656   -3.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2736   -3.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0907   -3.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8643   -2.4725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5000   -3.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0888   -4.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4973   -5.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3154   -5.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7232   -4.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3123   -3.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7255   -6.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5427   -6.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9529   -6.7092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9497   -5.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7669   -5.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  6  5  2  0
  7  6  2  0
  8  9  2  0
  9 10  1  0
 10 13  2  0
 12 11  2  0
 11  8  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15  6  1  0
  6 12  1  0
 14 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31  1  1  0
M  CHG  2   2   1   3  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4281901

   ---

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: 449.40

Molecular Weight (Monoisotopic): 449.0529

AlogP: 0.97

#Rotatable Bonds: 8

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: 1.31

CX LogD: 1.31

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: -1.60

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