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

ID: ALA300362

PubChem CID: 10670896

Max Phase: Preclinical

Molecular Formula: C16H15ClN4O7S

Molecular Weight: 442.84

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H15ClN4O7S/c17-12-3-7-14(8-4-12)29(27,28)19-16(23)20(10-15(22)18-24)9-11-1-5-13(6-2-11)21(25)26/h1-8,24H,9-10H2,(H,18,22)(H,19,23)

Standard InChI Key:  YRUNEWMUGNJMAR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    6.0500   -7.6417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -7.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -6.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -4.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -6.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -7.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -6.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -8.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3500   -7.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5750   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -6.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -4.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -4.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0500   -6.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -5.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -6.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -5.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -8.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792   -7.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5750   -5.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -4.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -5.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6000   -8.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0500   -5.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6000   -7.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792   -8.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -8.8292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -5.5250    0.0000 O   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 20  2  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 25  1  0
 21 24  2  0
 22 15  1  0
 23 26  1  0
 24 22  1  0
 25 22  2  0
 26 19  2  0
 27 18  1  0
 28 23  1  0
 29 17  1  0
 27 23  2  0
 21 10  1  0
M  CHG  2   4   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA300362

   2-[1-(4-nitro-benzyl)-(sulfonyl-(4-chlorobenzene))-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: 442.84

Molecular Weight (Monoisotopic): 442.0350

AlogP: 1.65

#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: 3.24

CX Basic pKa: ┄

CX LogP: 1.62

CX LogD: 0.66

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: -1.57

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