{5-[Hydroxycarbamoylmethyl-(4-nitro-benzyl)-sulfamoyl]-2-methoxy-phenyl}-carbamic acid tert-butyl ester

ID: ALA301977

PubChem CID: 10839419

Max Phase: Preclinical

Molecular Formula: C21H26N4O9S

Molecular Weight: 510.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N(CC(=O)NO)Cc2ccc([N+](=O)[O-])cc2)cc1NC(=O)OC(C)(C)C

Standard InChI:  InChI=1S/C21H26N4O9S/c1-21(2,3)34-20(27)22-17-11-16(9-10-18(17)33-4)35(31,32)24(13-19(26)23-28)12-14-5-7-15(8-6-14)25(29)30/h5-11,28H,12-13H2,1-4H3,(H,22,27)(H,23,26)

Standard InChI Key:  ATNNMKHWMHMLHP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
    5.0417   -7.1792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -6.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -5.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -7.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -6.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -7.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -7.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750   -7.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -6.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -7.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -6.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7375   -7.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0875   -5.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -5.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -6.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -4.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6500   -6.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -8.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -6.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -8.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -7.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -6.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -8.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1667   -6.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0875   -5.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -5.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -6.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -5.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -8.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -5.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1750   -7.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6917   -6.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6917   -6.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6500   -8.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 13  1  0
  4  1  1  0
  5 10  1  0
  6  2  1  0
  7  8  2  0
  8  4  1  0
  9  6  1  0
 10  7  1  0
 11  1  2  0
 12  1  2  0
 13 26  1  0
 14  3  1  0
 15  2  1  0
 16  3  2  0
 17  5  1  0
 18 23  2  0
 19  5  2  0
 20  4  2  0
 21  9  2  0
 22  9  1  0
 23 20  1  0
 24 17  1  0
 25 28  1  0
 26 29  2  0
 27 15  1  0
 28 27  2  0
 29 27  1  0
 30 18  1  0
 31 22  1  0
 32 24  1  0
 33 24  1  0
 34 24  1  0
 35 30  1  0
  7 18  1  0
 25 13  2  0
M  CHG  2   3   1  14  -1
M  END

Alternative Forms

1. Parent:

   

   ALA301977

   {5-[Hydroxycarbamoylmethyl-(4-nitro-benzyl)-sulfamoyl]-2-methoxy-phenyl}-carbamic acid tert-butyl ester

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: 510.53

Molecular Weight (Monoisotopic): 510.1420

AlogP: 2.65

#Rotatable Bonds: 9

Polar Surface Area: 177.41

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.74

CX Basic pKa: ┄

CX LogP: 2.11

CX LogD: 2.09

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.26

Np Likeness Score: -1.66

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