N-Hydroxy-2-[(3-nitro-benzenesulfonyl)-(4-nitro-benzyl)-amino]-acetamide

ID: ALA53044

PubChem CID: 11795824

Max Phase: Preclinical

Molecular Formula: C15H14N4O8S

Molecular Weight: 410.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN(Cc1ccc([N+](=O)[O-])cc1)S(=O)(=O)c1cccc([N+](=O)[O-])c1)NO

Standard InChI:  InChI=1S/C15H14N4O8S/c20-15(16-21)10-17(9-11-4-6-12(7-5-11)18(22)23)28(26,27)14-3-1-2-13(8-14)19(24)25/h1-8,21H,9-10H2,(H,16,20)

Standard InChI Key:  WPXAJFJACNOICK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    5.4375   -7.2250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -6.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -7.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -5.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9625   -7.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -7.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -6.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -7.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0000   -7.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375   -7.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7500   -6.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0542   -7.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -5.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -6.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5250   -6.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -4.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -7.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -6.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9542   -5.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9625   -6.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -6.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9542   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -8.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  9  1  0
  4 12  1  0
  5  1  1  0
  6  2  1  0
  7  6  1  0
  8  5  1  0
  9  8  2  0
 10  1  2  0
 11  1  2  0
 12 21  2  0
 13  3  1  0
 14  4  1  0
 15  2  1  0
 16  3  2  0
 17  4  2  0
 18  7  2  0
 19  7  1  0
 20 23  2  0
 21 24  1  0
 22 15  1  0
 23 22  1  0
 24 22  2  0
 25 19  1  0
 26  5  2  0
 27 28  2  0
 28 26  1  0
  9 27  1  0
 12 20  1  0
M  CHG  4   3   1   4   1  13  -1  14  -1
M  END

Alternative Forms

1. Parent:

   

   ALA53044

   N-Hydroxy-2-[(3-nitro-benzenesulfonyl)-(4-nitro-benzyl)-amino]-acetamide

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: 410.36

Molecular Weight (Monoisotopic): 410.0532

AlogP: 1.20

#Rotatable Bonds: 8

Polar Surface Area: 172.99

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.74

CX Basic pKa: ┄

CX LogP: 1.30

CX LogD: 1.28

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.37

Np Likeness Score: -1.77

References

1. Scozzafava A, Supuran CT..  (2000)  Protease inhibitors: synthesis of potent bacterial collagenase and matrix metalloproteinase inhibitors incorporating N-4-nitrobenzylsulfonylglycine hydroxamate moieties.,  43  (9): [PMID:10794702] [10.1021/jm990594k]

Source

Source(1):

• Scientific Literature