N-Hydroxy-2-[(4-nitro-benzyl)-(3-trifluoromethyl-benzenesulfonyl)-amino]-acetamide

ID: ALA54054

PubChem CID: 10365560

Max Phase: Preclinical

Molecular Formula: C16H14F3N3O6S

Molecular Weight: 433.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN(Cc1ccc([N+](=O)[O-])cc1)S(=O)(=O)c1cccc(C(F)(F)F)c1)NO

Standard InChI:  InChI=1S/C16H14F3N3O6S/c17-16(18,19)12-2-1-3-14(8-12)29(27,28)21(10-15(23)20-24)9-11-4-6-13(7-5-11)22(25)26/h1-8,24H,9-10H2,(H,20,23)

Standard InChI Key:  FEWWJFPIJXNCFE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    5.5667   -7.2250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -6.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -5.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542   -7.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -7.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -7.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -6.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -7.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -7.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2625   -7.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -6.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6125   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542   -5.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -6.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -4.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -7.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -6.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1750   -7.5167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -6.6042    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.1750   -6.9125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.6125   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -5.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -6.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -6.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -8.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 12  1  0
  4  8  1  0
  5  1  1  0
  6  2  1  0
  7  6  1  0
  8  9  2  0
  9  5  1  0
 10  1  2  0
 11  1  2  0
 12 22  1  0
 13  3  1  0
 14  2  1  0
 15  3  2  0
 16  7  2  0
 17  7  1  0
 18  4  1  0
 19  4  1  0
 20  4  1  0
 21 24  1  0
 22 25  2  0
 23 14  1  0
 24 23  2  0
 25 23  1  0
 26 17  1  0
 27  5  2  0
 28 29  2  0
 29 27  1  0
  8 28  1  0
 21 12  2  0
M  CHG  2   3   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA54054

   N-Hydroxy-2-[(4-nitro-benzyl)-(3-trifluoromethyl-benzenesulfonyl)-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: 433.36

Molecular Weight (Monoisotopic): 433.0555

AlogP: 2.31

#Rotatable Bonds: 7

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: 2.24

CX LogD: 2.22

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: -1.98

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