2-[(N,N dimethyl-1-sulfonyl)-(4-nitro-benzyl)-amino]-N-hydroxy-acetamide

ID: ALA55107

PubChem CID: 10640307

Max Phase: Preclinical

Molecular Formula: C11H16N4O6S

Molecular Weight: 332.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H16N4O6S/c1-13(2)22(20,21)14(8-11(16)12-17)7-9-3-5-10(6-4-9)15(18)19/h3-6,17H,7-8H2,1-2H3,(H,12,16)

Standard InChI Key:  OPYOHFRGHGDNSJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    5.7042   -7.3792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -7.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -5.2625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -7.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -7.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -7.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -7.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -6.8625    0.0000 O   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
    7.7917   -5.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -6.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -4.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -7.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -6.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -6.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -5.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -6.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -6.4667    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
    3.6125   -6.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -8.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -7.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  9  1  0
  4  2  1  0
  5  4  1  0
  6  1  1  0
  7  1  2  0
  8  1  2  0
  9 16  1  0
 10  3  1  0
 11  2  1  0
 12  3  2  0
 13  5  2  0
 14  5  1  0
 15 18  1  0
 16 19  2  0
 17 11  1  0
 18 17  2  0
 19 17  1  0
 20 14  1  0
 21  6  1  0
 22  6  1  0
 15  9  2  0
M  CHG  2   3   1  10  -1
M  END

Alternative Forms

1. Parent:

   

   ALA55107

   2-[(N,N dimethyl-1-sulfonyl)-(4-nitro-benzyl)-amino]-N-hydroxy-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: 332.34

Molecular Weight (Monoisotopic): 332.0791

AlogP: -0.29

#Rotatable Bonds: 7

Polar Surface Area: 133.09

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.74

CX Basic pKa: ┄

CX LogP: -0.76

CX LogD: -0.78

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.40

Np Likeness Score: -1.53

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