(S)-N-((S)-3-amino-1-cyano-3-oxopropyl)-1-((4'-methoxy-[1,1'-biphenyl]-4-yl)sulfonyl)pyrrolidine-2-carboxamide

ID: ALA3740153

PubChem CID: 127042051

Max Phase: Preclinical

Molecular Formula: C22H24N4O5S

Molecular Weight: 456.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2ccc(S(=O)(=O)N3CCC[C@H]3C(=O)N[C@H](C#N)CC(N)=O)cc2)cc1

Standard InChI:  InChI=1S/C22H24N4O5S/c1-31-18-8-4-15(5-9-18)16-6-10-19(11-7-16)32(29,30)26-12-2-3-20(26)22(28)25-17(14-23)13-21(24)27/h4-11,17,20H,2-3,12-13H2,1H3,(H2,24,27)(H,25,28)/t17-,20-/m0/s1

Standard InChI Key:  UROMPZIPIORZKO-PXNSSMCTSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    2.5984   -2.7004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.5004    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6377   -2.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5052    1.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2543   -0.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2499   -1.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0377    0.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5461   -2.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4210   -3.8346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6836   -3.2237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7177   -5.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1403   -5.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925   -6.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8892   -7.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266   -8.1526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9896   -8.5644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2777   -6.1664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015    3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5018    3.7420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5392    3.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  6  5  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  6  9  1  1
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  6
 14 15  1  0
 15 16  1  0
 15 17  2  0
 13 18  3  0
  7  2  1  0
  2 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 22 25  1  0
 28 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3740153

   ---

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: 456.52

Molecular Weight (Monoisotopic): 456.1467

AlogP: 1.40

#Rotatable Bonds: 8

Polar Surface Area: 142.59

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.20

CX Basic pKa: ┄

CX LogP: 0.68

CX LogD: 0.68

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.61

Np Likeness Score: -1.20

References

1. Ness KA, Eddie SL, Higgins CA, Templeman A, D'Costa Z, Gaddale KK, Bouzzaoui S, Jordan L, Janssen D, Harrison T, Burkamp F, Young A, Burden R, Scott CJ, Mullan PB, Williams R..  (2015)  Development of a potent and selective cell penetrant Legumain inhibitor.,  25  (23): [PMID:26522952] [10.1016/j.bmcl.2015.10.001]

Source

Source(1):

• Scientific Literature