(S)-2-sec-Butyl-3-oxo-4-(toluene-4-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester

ID: ALA126390

PubChem CID: 44350497

Max Phase: Preclinical

Molecular Formula: C20H30N2O5S

Molecular Weight: 410.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)[C@H]1C(=O)N(S(=O)(=O)c2ccc(C)cc2)CCN1C(=O)OC(C)(C)C

Standard InChI:  InChI=1S/C20H30N2O5S/c1-7-15(3)17-18(23)22(13-12-21(17)19(24)27-20(4,5)6)28(25,26)16-10-8-14(2)9-11-16/h8-11,15,17H,7,12-13H2,1-6H3/t15?,17-/m0/s1

Standard InChI Key:  KUPBCMLJUYZXEQ-LWKPJOBUSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  1  0  0  0  0  0999 V2000
    4.4000   -2.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -1.8875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -3.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -4.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -5.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -3.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875   -5.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -1.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -1.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292   -2.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -5.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -6.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -0.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292   -4.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667    0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000    0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792    0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -6.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875   -6.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875   -7.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292   -5.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750    1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -4.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  8  1  0
  5  4  1  0
  6  3  1  0
  7  1  1  0
  8  7  1  0
  9  2  1  0
 10  5  1  0
 11  2  2  0
 12  2  2  0
 13  3  2  0
 14  5  2  0
 15 10  1  0
 16  9  2  0
 17  9  1  0
  6 18  1  6
 19 17  2  0
 20 16  1  0
 21 19  1  0
 22 15  1  0
 23 15  1  0
 24 15  1  0
 25 18  1  0
 26 18  1  0
 27 21  1  0
 28 25  1  0
  4  6  1  0
 21 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA126390

   (S)-2-sec-Butyl-3-oxo-4-(toluene-4-sulfonyl)-piperazine-1-carboxylic 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: 410.54

Molecular Weight (Monoisotopic): 410.1875

AlogP: 3.18

#Rotatable Bonds: 4

Polar Surface Area: 83.99

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.76

Np Likeness Score: -0.85

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