2-[1-(4-nitro-benzyl)-(sulfonyl-(4-methylbenzene))-ureido]-N-Hydroxy-acetamide

ID: ALA52531

PubChem CID: 10550145

Max Phase: Preclinical

Molecular Formula: C17H18N4O7S

Molecular Weight: 422.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)NC(=O)N(CC(=O)NO)Cc2ccc([N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C17H18N4O7S/c1-12-2-8-15(9-3-12)29(27,28)19-17(23)20(11-16(22)18-24)10-13-4-6-14(7-5-13)21(25)26/h2-9,24H,10-11H2,1H3,(H,18,22)(H,19,23)

Standard InChI Key:  WEACEEZKOJLZFG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    6.0917   -7.6875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -7.3875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -6.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1375   -4.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0500   -6.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -7.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -6.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7875   -8.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -7.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6167   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -6.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6625   -4.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1375   -4.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -6.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0500   -5.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -6.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -5.8750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -8.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1250   -7.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6167   -5.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0875   -4.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -5.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -5.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -7.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1250   -8.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -8.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -5.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1667   -8.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4 10  1  0
  5  3  1  0
  6  1  1  0
  7 11  1  0
  8  1  2  0
  9  1  2  0
 10 21  1  0
 11  5  1  0
 12  4  1  0
 13  4  2  0
 14  3  2  0
 15  5  1  0
 16  7  2  0
 17  7  1  0
 18  6  2  0
 19  6  1  0
 20 23  1  0
 21 24  2  0
 22 15  1  0
 23 22  2  0
 24 22  1  0
 25 19  2  0
 26 18  1  0
 27 25  1  0
 28 17  1  0
 29 27  1  0
 26 27  2  0
 20 10  2  0
M  CHG  2   4   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA52531

   2-[1-(4-nitro-benzyl)-(sulfonyl-(4-methylbenzene))-ureido]-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: 422.42

Molecular Weight (Monoisotopic): 422.0896

AlogP: 1.31

#Rotatable Bonds: 7

Polar Surface Area: 158.95

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.25

CX Basic pKa: ┄

CX LogP: 1.53

CX LogD: 0.57

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: -1.48

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