N-Hydroxy-2-[(4-nitro-benzyl)-(3-(N-(4-Chloro-benzene)-sulfonyl)ureido-benzenesulfonyl)-amino]-acetamide

ID: ALA55522

PubChem CID: 10698786

Max Phase: Preclinical

Molecular Formula: C22H20ClN5O9S2

Molecular Weight: 598.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN(Cc1ccc([N+](=O)[O-])cc1)S(=O)(=O)c1cccc(NC(=O)NS(=O)(=O)c2ccc(Cl)cc2)c1)NO

Standard InChI:  InChI=1S/C22H20ClN5O9S2/c23-16-6-10-19(11-7-16)38(34,35)26-22(30)24-17-2-1-3-20(12-17)39(36,37)27(14-21(29)25-31)13-15-4-8-18(9-5-15)28(32)33/h1-12,31H,13-14H2,(H,25,29)(H2,24,26,30)

Standard InChI Key:  HGCCQMHYESJBML-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 41  0  0  0  0  0  0  0  0999 V2000
    3.8667   -7.2292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -7.2417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9667   -7.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -5.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5000   -7.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -7.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -7.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -6.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5542   -7.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -6.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7417   -6.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9542   -5.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2917   -6.3250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1875   -8.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5542   -7.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9125   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2167   -7.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875   -6.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542   -8.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1167   -7.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7875   -8.0917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7750   -6.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -8.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917   -8.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4125   -8.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  6  1  0
  5 14  1  0
  6 17  1  0
  7  1  1  0
  8  3  1  0
  9  8  1  0
 10  2  1  0
 11  1  2  0
 12  1  2  0
 13  7  1  0
 14 28  1  0
 15  2  2  0
 16  2  2  0
 17 21  1  0
 18  5  1  0
 19  3  1  0
 20  5  2  0
 21 13  2  0
 22  6  2  0
 23  9  2  0
 24  9  1  0
 25 10  2  0
 26 10  1  0
 27 31  1  0
 28 32  2  0
 29 19  1  0
 30 34  1  0
 31 29  2  0
 32 29  1  0
 33 25  1  0
 34 26  2  0
 35 30  1  0
 36 24  1  0
 37  7  2  0
 38 37  1  0
 39 38  2  0
 21 39  1  0
 27 14  2  0
 33 30  2  0
M  CHG  2   5   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA55522

   2-[[3-[(4-chlorophenyl)sulfonylcarbamoylamino]phenyl]sulfonyl-[(4-nitrophenyl)methyl]amino]-N-hydroxyacetamide

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: 598.02

Molecular Weight (Monoisotopic): 597.0391

AlogP: 2.45

#Rotatable Bonds: 10

Polar Surface Area: 205.12

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.60

CX Basic pKa: ┄

CX LogP: 2.47

CX LogD: 1.50

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.15

Np Likeness Score: -1.89

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