N-Hydroxy-2-[(4-nitro-benzyl)-(4-nitro-phenylsulfanyl)-amino]-acetamide

ID: ALA292431

PubChem CID: 10595804

Max Phase: Preclinical

Molecular Formula: C15H14N4O6S

Molecular Weight: 378.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN(Cc1ccc([N+](=O)[O-])cc1)Sc1ccc([N+](=O)[O-])cc1)NO

Standard InChI:  InChI=1S/C15H14N4O6S/c20-15(16-21)10-17(9-11-1-3-12(4-2-11)18(22)23)26-14-7-5-13(6-8-14)19(24)25/h1-8,21H,9-10H2,(H,16,20)

Standard InChI Key:  DCSHLVVGHNRVCO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    7.2542   -4.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -8.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -6.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375   -6.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -6.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -8.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7375   -4.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7750   -4.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -9.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -6.4250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542   -3.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2250   -9.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -6.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375   -5.5250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -5.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -7.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2125   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -7.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7375   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -7.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -7.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -7.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -4.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -5.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -5.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3 15  1  0
  4  5  1  0
  5  3  1  0
  6 18  2  0
  7  1  1  0
  8  1  1  0
  9  2  1  0
 10  3  1  0
 11  1  2  0
 12  2  2  0
 13  4  2  0
 14  4  1  0
 15 21  1  0
 16 22  2  0
 17  7  1  0
 18 23  1  0
 19  7  2  0
 20 10  1  0
 21 25  2  0
 22 20  1  0
 23 20  2  0
 24 17  2  0
 25 19  1  0
 26 14  1  0
 24 21  1  0
 16  6  1  0
M  CHG  4   1   1   2   1   8  -1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA292431

   N-Hydroxy-2-[(4-nitro-benzyl)-(4-nitro-phenylsulfanyl)-amino]-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: 378.37

Molecular Weight (Monoisotopic): 378.0634

AlogP: 2.52

#Rotatable Bonds: 8

Polar Surface Area: 138.85

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.75

CX Basic pKa: ┄

CX LogP: 2.21

CX LogD: 2.19

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.31

Np Likeness Score: -0.83

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