[(4-Nitro-benzyl)-(3-(N-(4-Fluoro-benzene)sulfonyl)-ureido-benzenesulfonyl)-amino]-acetic acid

ID: ALA301177

PubChem CID: 10650624

Max Phase: Preclinical

Molecular Formula: C22H19FN4O9S2

Molecular Weight: 566.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CN(Cc1ccc([N+](=O)[O-])cc1)S(=O)(=O)c1cccc(NC(=O)NS(=O)(=O)c2ccc(F)cc2)c1

Standard InChI:  InChI=1S/C22H19FN4O9S2/c23-16-6-10-19(11-7-16)37(33,34)25-22(30)24-17-2-1-3-20(12-17)38(35,36)26(14-21(28)29)13-15-4-8-18(9-5-15)27(31)32/h1-12H,13-14H2,(H,28,29)(H2,24,25,30)

Standard InChI Key:  YDCLZJDJJGSFJZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 38 40  0  0  0  0  0  0  0  0999 V2000
    3.9000   -7.2292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.5667   -7.2167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -6.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9917   -7.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667   -5.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417   -7.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -7.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -7.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1375   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -7.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -6.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -6.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -7.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7667   -6.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3750   -7.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -7.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -5.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -6.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667   -4.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -7.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -8.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042   -7.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5917   -7.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -8.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -6.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -6.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2667   -7.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -6.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4292   -6.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8042   -8.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1542   -7.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8417   -8.0292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -8.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  6  1  0
  5 14  1  0
  6 17  1  0
  7  1  1  0
  8  3  1  0
  9  2  1  0
 10  1  2  0
 11  1  2  0
 12  8  1  0
 13  7  1  0
 14 27  2  0
 15  2  2  0
 16  2  2  0
 17 21  1  0
 18  5  1  0
 19  3  1  0
 20  5  2  0
 21 13  2  0
 22  6  2  0
 23 12  2  0
 24  9  1  0
 25  9  2  0
 26 31  2  0
 27 32  1  0
 28 19  1  0
 29 33  2  0
 30 12  1  0
 31 28  1  0
 32 28  2  0
 33 25  1  0
 34 24  2  0
 35 29  1  0
 36  7  2  0
 37 36  1  0
 38 37  2  0
 21 38  1  0
 26 14  1  0
 34 29  1  0
M  CHG  2   5   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA301177

   2-[[3-[(4-Fluorophenyl)sulfonylcarbamoylamino]phenyl]sulfonyl-[(4-nitrophenyl)methyl]amino]acetic acid

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: 566.55

Molecular Weight (Monoisotopic): 566.0577

AlogP: 2.52

#Rotatable Bonds: 10

Polar Surface Area: 193.09

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.36

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: -1.63

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.24

Np Likeness Score: -1.91

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