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

ID: ALA53009

PubChem CID: 10721337

Max Phase: Preclinical

Molecular Formula: C22H20N4O9S2

Molecular Weight: 548.56

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)c2ccccc2)c1

Standard InChI:  InChI=1S/C22H20N4O9S2/c27-21(28)15-25(14-16-9-11-18(12-10-16)26(30)31)37(34,35)20-8-4-5-17(13-20)23-22(29)24-36(32,33)19-6-2-1-3-7-19/h1-13H,14-15H2,(H,27,28)(H2,23,24,29)

Standard InChI Key:  RTBPRRSADWSXAD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
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    7.8500   -7.2167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -6.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2792   -7.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7500   -5.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -7.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1417   -7.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -7.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -6.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2167   -7.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0542   -6.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6500   -7.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542   -7.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7042   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -6.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -6.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -6.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -6.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -8.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5292   -8.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8667   -7.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4375   -7.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0917   -8.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500   -7.8250    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 13  1  0
  6 16  1  0
  7  1  1  0
  8  3  1  0
  9  1  2  0
 10  1  2  0
 11  8  1  0
 12  7  1  0
 13 25  2  0
 14  2  2  0
 15  2  2  0
 16 21  1  0
 17  2  1  0
 18  5  1  0
 19  3  1  0
 20  5  2  0
 21 12  2  0
 22  6  2  0
 23 11  2  0
 24 28  2  0
 25 29  1  0
 26 19  1  0
 27 11  1  0
 28 26  1  0
 29 26  2  0
 30  7  2  0
 31 30  1  0
 32 31  2  0
 33 17  2  0
 34 17  1  0
 35 34  2  0
 36 33  1  0
 37 35  1  0
 21 32  1  0
 24 13  1  0
 36 37  2  0
M  CHG  2   5   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA53009

   [(4-Nitro-benzyl)-(3-(N-benzene sulfonyl)-ureido-benzenesulfonyl)-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: 548.56

Molecular Weight (Monoisotopic): 548.0672

AlogP: 2.38

#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: 2.67

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: -1.77

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.25

Np Likeness Score: -1.69

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