N-Hydroxy-2-[(4-nitro-benzyl)-(2,4,6-trimethyl-benzenesulfonyl)-amino]-acetamide

ID: ALA299091

PubChem CID: 10597516

Max Phase: Preclinical

Molecular Formula: C18H21N3O6S

Molecular Weight: 407.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)c(S(=O)(=O)N(CC(=O)NO)Cc2ccc([N+](=O)[O-])cc2)c(C)c1

Standard InChI:  InChI=1S/C18H21N3O6S/c1-12-8-13(2)18(14(3)9-12)28(26,27)20(11-17(22)19-23)10-15-4-6-16(7-5-15)21(24)25/h4-9,23H,10-11H2,1-3H3,(H,19,22)

Standard InChI Key:  QFPRVWUEWDLNPU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    5.7000   -7.2250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -6.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -7.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -5.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -7.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -7.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -6.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -6.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -7.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -5.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -6.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -4.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -7.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -8.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -7.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -6.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -5.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -6.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -6.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -8.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875   -8.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4 11  1  0
  5  2  1  0
  6  3  2  0
  7  3  1  0
  8  5  1  0
  9  1  2  0
 10  1  2  0
 11 21  2  0
 12  4  1  0
 13  2  1  0
 14  4  2  0
 15  7  2  0
 16  6  1  0
 17  8  2  0
 18 15  1  0
 19  8  1  0
 20 23  2  0
 21 24  1  0
 22 13  1  0
 23 22  1  0
 24 22  2  0
 25 19  1  0
 26  7  1  0
 27  6  1  0
 28 18  1  0
 16 18  2  0
 11 20  1  0
M  CHG  2   4   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA299091

   N-Hydroxy-2-[(4-nitro-benzyl)-(2,4,6-trimethyl-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: 407.45

Molecular Weight (Monoisotopic): 407.1151

AlogP: 2.22

#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: 2.90

CX LogD: 2.88

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -1.56

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