(S)-1-Benzyl-3-sec-butyl-4-(toluene-4-sulfonyl)-piperazin-2-one

ID: ALA126245

PubChem CID: 44350346

Max Phase: Preclinical

Molecular Formula: C22H28N2O3S

Molecular Weight: 400.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)[C@H]1C(=O)N(Cc2ccccc2)CCN1S(=O)(=O)c1ccc(C)cc1

Standard InChI:  InChI=1S/C22H28N2O3S/c1-4-18(3)21-22(25)23(16-19-8-6-5-7-9-19)14-15-24(21)28(26,27)20-12-10-17(2)11-13-20/h5-13,18,21H,4,14-16H2,1-3H3/t18?,21-/m0/s1

Standard InChI Key:  BXHNHHNZVPVMOA-ZYZRXSCRSA-N

Molfile:  

     RDKit          2D

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    0.2375   -3.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2375   -1.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -5.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625   -4.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -4.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2375   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -1.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -3.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375   -5.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -6.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958   -6.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2125   -6.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -7.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -1.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917   -3.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5 10  1  0
  6  2  1  0
  7  1  1  0
  8  1  2  0
  9  1  2  0
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 12  4  2  0
  3 13  1  6
 14  7  2  0
 15  7  1  0
 16 11  1  0
 17 15  2  0
 18 14  1  0
 19 17  1  0
 20 13  1  0
 21 13  1  0
 22 19  1  0
 23 16  2  0
 24 16  1  0
 25 20  1  0
 26 24  2  0
 27 23  1  0
 28 26  1  0
 19 18  2  0
  5  4  1  0
 28 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA126245

   (3S)-1-benzyl-3-butan-2-yl-4-(4-methylphenyl)sulfonylpiperazin-2-one

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: 400.54

Molecular Weight (Monoisotopic): 400.1821

AlogP: 3.44

#Rotatable Bonds: 6

Polar Surface Area: 57.69

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.11

CX LogD: 4.11

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.75

Np Likeness Score: -0.94

References

1. Seibel J, Brown D, Amour A, Macdonald SJ, Oldham NJ, Schofield CJ..  (2003)  Synthesis and evaluation of delta-lactams (piperazones) as elastase inhibitors.,  13  (3): [PMID:12565935] [10.1016/s0960-894x(02)00995-2]

Source

Source(1):

• Scientific Literature