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

ID: ALA53091

PubChem CID: 10762262

Max Phase: Preclinical

Molecular Formula: C16H17N3O6S

Molecular Weight: 379.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN(Cc1ccc([N+](=O)[O-])cc1)S(=O)(=O)Cc1ccccc1)NO

Standard InChI:  InChI=1S/C16H17N3O6S/c20-16(17-21)11-18(10-13-6-8-15(9-7-13)19(22)23)26(24,25)12-14-4-2-1-3-5-14/h1-9,21H,10-12H2,(H,17,20)

Standard InChI Key:  YTZCQIFAVXLXHV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    5.7042   -6.7750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -4.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -6.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -6.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -6.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -7.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -4.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -6.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -7.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -4.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -4.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -5.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -6.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -5.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -5.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -5.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -7.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -4.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -5.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -5.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -7.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -7.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -8.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -8.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -8.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3  1  1  0
  4  3  1  0
  5  4  1  0
  6  1  1  0
  7 15  2  0
  8  1  2  0
  9  1  2  0
 10  2  1  0
 11  2  2  0
 12  3  1  0
 13  5  2  0
 14  5  1  0
 15 20  1  0
 16 19  2  0
 17 12  1  0
 18  6  1  0
 19 17  1  0
 20 17  2  0
 21 14  1  0
 22 18  2  0
 23 18  1  0
 24 23  2  0
 25 22  1  0
 26 24  1  0
 25 26  2  0
  7 16  1  0
M  CHG  2   2   1  10  -1
M  END

Alternative Forms

1. Parent:

   

   ALA53091

   N-Hydroxy-2-[(4-nitro-benzyl)-phenylmethanesulfonyl-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: 379.39

Molecular Weight (Monoisotopic): 379.0838

AlogP: 1.43

#Rotatable Bonds: 8

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: 1.12

CX LogD: 1.10

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.41

Np Likeness Score: -1.47

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