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

ID: ALA3741594

PubChem CID: 127037715

Max Phase: Preclinical

Molecular Formula: C25H30N4O4S

Molecular Weight: 482.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(-c2ccc(S(=O)(=O)N3CCC[C@H]3C(=O)N[C@H](C#N)CC(N)=O)cc2)cc1

Standard InChI:  InChI=1S/C25H30N4O4S/c1-25(2,3)19-10-6-17(7-11-19)18-8-12-21(13-9-18)34(32,33)29-14-4-5-22(29)24(31)28-20(16-26)15-23(27)30/h6-13,20,22H,4-5,14-15H2,1-3H3,(H2,27,30)(H,28,31)/t20-,22-/m0/s1

Standard InChI Key:  ZWNFXBJAGVYQIA-UNMCSNQZSA-N

Molfile:  

     RDKit          2D

 34 36  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
   -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
   -5.1993    2.9963    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
   -6.5002    3.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5389    3.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5018    4.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5401    4.3435    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 30  1  0
 29 27  1  0
 27 28  2  0
 28 25  1  0
 22 25  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3741594

   ---

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: 482.61

Molecular Weight (Monoisotopic): 482.1988

AlogP: 2.69

#Rotatable Bonds: 7

Polar Surface Area: 133.36

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.22

CX Basic pKa: ┄

CX LogP: 2.39

CX LogD: 2.39

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.63

Np Likeness Score: -1.31

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]

2. Eddie SL, Gregson A, Graham E, Burton S, Harrison T, Burden R, Scott CJ, Mullan PB, Williams R..  (2019)  Identification and SAR exploration of a novel series of Legumain inhibitors.,  29  (12): [PMID:31005445] [10.1016/j.bmcl.2019.03.019]

Source

Source(1):

• Scientific Literature