1-benzyl-N-hydroxy-3-((4-methoxyphenyl)sulfonyl)-6-oxohexahydropyrimidine-4-carboxamide

ID: ALA437017

Max Phase: Preclinical

Molecular Formula: C19H21N3O6S

Molecular Weight: 419.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N2CN(Cc3ccccc3)C(=O)CC2C(=O)NO)cc1

Standard InChI:  InChI=1S/C19H21N3O6S/c1-28-15-7-9-16(10-8-15)29(26,27)22-13-21(12-14-5-3-2-4-6-14)18(23)11-17(22)19(24)20-25/h2-10,17,25H,11-13H2,1H3,(H,20,24)

Standard InChI Key:  SUSMVCKSLVPRCL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.7083  -21.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083  -21.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9963  -22.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843  -21.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843  -21.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9963  -20.6458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5704  -22.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9963  -19.8208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0042  -18.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1713  -19.8169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8213  -19.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2913  -18.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2988  -17.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177  -17.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7306  -17.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7196  -18.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0267  -16.5227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3167  -16.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4240  -20.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4264  -19.8271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1373  -21.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8529  -20.6563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9963  -23.1208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5716  -23.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877  -23.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2893  -24.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749  -24.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1426  -24.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1406  -23.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0
 14 15  1  0
  1  2  1  0
 15 16  2  0
 16  9  1  0
  6  8  1  0
 14 17  1  0
  1  6  1  0
 17 18  1  0
  8  9  1  0
  1 19  1  0
  2  3  1  0
 19 20  2  0
  8 10  2  0
 19 21  1  0
  3  4  1  0
 21 22  1  0
  8 11  2  0
  3 23  2  0
  4  5  1  0
  7 24  1  0
  9 12  2  0
 24 25  2  0
  5  6  1  0
 25 26  1  0
 12 13  1  0
 26 27  2  0
 27 28  1  0
 13 14  2  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA437017

   ---

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: 419.46

Molecular Weight (Monoisotopic): 419.1151

AlogP: 0.95

#Rotatable Bonds: 6

Polar Surface Area: 116.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.71

CX Basic pKa: ┄

CX LogP: 0.77

CX LogD: 0.75

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -1.06

References

1. Mondal S, Adhikari N, Banerjee S, Amin SA, Jha T..  (2020)  Matrix metalloproteinase-9 (MMP-9) and its inhibitors in cancer: A minireview.,  194  [PMID:32224379] [10.1016/j.ejmech.2020.112260]

Source

Source(1):

• Scientific Literature