2-[(2,5-Dichloro-benzenesulfonyl)-(4-nitro-benzyl)-amino]-N-hydroxy-acetamide

ID: ALA301786

PubChem CID: 10741470

Max Phase: Preclinical

Molecular Formula: C15H13Cl2N3O6S

Molecular Weight: 434.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN(Cc1ccc([N+](=O)[O-])cc1)S(=O)(=O)c1cc(Cl)ccc1Cl)NO

Standard InChI:  InChI=1S/C15H13Cl2N3O6S/c16-11-3-6-13(17)14(7-11)27(25,26)19(9-15(21)18-22)8-10-1-4-12(5-2-10)20(23)24/h1-7,22H,8-9H2,(H,18,21)

Standard InChI Key:  MZISFPSOTJFTTJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    5.7000   -6.8792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -7.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -6.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -4.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -6.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -7.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -7.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -6.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -6.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -5.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -5.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -4.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -6.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -5.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -4.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -7.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -8.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -6.2667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -7.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -5.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -8.6875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -5.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4 11  1  0
  5  3  1  0
  6  5  1  0
  7  2  2  0
  8  1  2  0
  9  1  2  0
 10  2  1  0
 11 18  1  0
 12  4  1  0
 13  3  1  0
 14  4  2  0
 15  6  2  0
 16  6  1  0
 17 24  1  0
 18 25  2  0
 19 10  2  0
 20  7  1  0
 21 13  1  0
 22 10  1  0
 23 19  1  0
 24 21  2  0
 25 21  1  0
 26 20  1  0
 27 16  1  0
 20 23  2  0
 17 11  2  0
M  CHG  2   4   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA301786

   2-[(2,5-Dichloro-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: 434.26

Molecular Weight (Monoisotopic): 432.9902

AlogP: 2.60

#Rotatable Bonds: 7

Polar Surface Area: 129.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.74

CX Basic pKa: ┄

CX LogP: 2.57

CX LogD: 2.55

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.39

Np Likeness Score: -2.02

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