N-((S,E)-5-phenyl-1-(phenylsulfonyl)pent-1-en-3-yl)pyrrolidine-2-carboxamide

ID: ALA1242747

PubChem CID: 23643997

Max Phase: Preclinical

Molecular Formula: C22H26N2O3S

Molecular Weight: 398.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H](/C=C/S(=O)(=O)c1ccccc1)CCc1ccccc1)C1CCCN1

Standard InChI:  InChI=1S/C22H26N2O3S/c25-22(21-12-7-16-23-21)24-19(14-13-18-8-3-1-4-9-18)15-17-28(26,27)20-10-5-2-6-11-20/h1-6,8-11,15,17,19,21,23H,7,12-14,16H2,(H,24,25)/b17-15+/t19-,21?/m0/s1

Standard InChI Key:  BGTATSBYSPZUSB-BNWRYQNMSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    3.7706   -9.0132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1805   -9.7292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5971   -9.0154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1064   -9.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6081  -10.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6081  -10.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3226   -9.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0371  -10.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515   -9.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0371  -10.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515  -11.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515  -12.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0340  -12.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336  -13.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486  -13.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655  -13.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4623  -12.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4660  -10.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8949  -10.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8931  -10.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6067  -11.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3221  -10.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3195  -10.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6053   -9.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974   -8.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0044   -8.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4169   -9.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8648  -10.0628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  4  5  1  0
 15 16  1  0
  8  9  1  0
 16 17  2  0
 17 12  1  0
  3  2  2  0
  9 18  2  0
 18  2  1  0
  8 10  1  6
  2 19  1  0
  5  6  2  0
 19 20  2  0
 10 11  1  0
 20 21  1  0
 21 22  2  0
 11 12  1  0
 22 23  1  0
  5  7  1  0
 23 24  2  0
 24 19  1  0
  4 25  1  0
 12 13  2  0
  2  1  2  0
 13 14  1  0
  7  8  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1242747

   N-((S,E)-5-Phenyl-1-(phenylsulfonyl)pent-1-en-3-yl)pyrrolidine-2-carboxamide

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: 398.53

Molecular Weight (Monoisotopic): 398.1664

AlogP: 2.84

#Rotatable Bonds: 8

Polar Surface Area: 75.27

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.61

CX LogP: 3.01

CX LogD: 0.84

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.72

Np Likeness Score: -0.08

References

1. Arastu-Kapur S, Ponder EL, Fonović UP, Yeoh S, Yuan F, Fonović M, Grainger M, Phillips CI, Powers JC, Bogyo M..  (2008)  Identification of proteases that regulate erythrocyte rupture by the malaria parasite Plasmodium falciparum.,  4  (3): [PMID:18246061] [10.1038/nchembio.70]

Source

Source(1):

• Scientific Literature