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

ID: ALA299600

PubChem CID: 10741956

Max Phase: Preclinical

Molecular Formula: C15H13ClN4O8S

Molecular Weight: 444.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN(Cc1ccc([N+](=O)[O-])cc1)S(=O)(=O)c1ccc([N+](=O)[O-])c(Cl)c1)NO

Standard InChI:  InChI=1S/C15H13ClN4O8S/c16-13-7-12(5-6-14(13)20(25)26)29(27,28)18(9-15(21)17-22)8-10-1-3-11(4-2-10)19(23)24/h1-7,22H,8-9H2,(H,17,21)

Standard InChI Key:  NJSAPXUDAYVTFL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    5.5625   -6.8792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -6.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6500   -8.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -7.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -4.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -7.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -6.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -7.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -6.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -8.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -7.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -6.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6500   -8.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6500   -5.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -5.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1792   -7.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -4.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750   -7.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -6.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875   -5.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750   -4.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6500   -6.8750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -5.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -5.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4 11  2  0
  5 14  1  0
  6  1  1  0
  7  2  1  0
  8  9  2  0
  9  6  1  0
 10  7  1  0
 11 20  1  0
 12  1  2  0
 13  1  2  0
 14 23  2  0
 15  3  1  0
 16  5  1  0
 17  2  1  0
 18  3  2  0
 19  5  2  0
 20  6  2  0
 21 10  2  0
 22 10  1  0
 23 28  1  0
 24 27  2  0
 25  8  1  0
 26 17  1  0
 27 26  1  0
 28 26  2  0
 29 22  1  0
  8  4  1  0
 14 24  1  0
M  CHG  4   3   1   5   1  15  -1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA299600

   2-[(3-Chloro-4-nitro-benzenesulfonyl)-(4-nitro-benzyl)-amino]-N-hydroxy-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: 444.81

Molecular Weight (Monoisotopic): 444.0143

AlogP: 1.85

#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: 1.90

CX LogD: 1.88

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.35

Np Likeness Score: -1.90

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