(S)-N-(3-amino-1-cyano-3-oxopropyl)-3-((4-(5-fluoropyridine-3-yl)phenyl)sulphonyl)-2,2-dimethylpropanamide

ID: ALA4538455

PubChem CID: 155549215

Max Phase: Preclinical

Molecular Formula: C20H21FN4O4S

Molecular Weight: 432.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(CS(=O)(=O)c1ccc(-c2cncc(F)c2)cc1)C(=O)N[C@H](C#N)CC(N)=O

Standard InChI:  InChI=1S/C20H21FN4O4S/c1-20(2,19(27)25-16(9-22)8-18(23)26)12-30(28,29)17-5-3-13(4-6-17)14-7-15(21)11-24-10-14/h3-7,10-11,16H,8,12H2,1-2H3,(H2,23,26)(H,25,27)/t16-/m0/s1

Standard InChI Key:  ISURLBXHWWQVTE-INIZCTEOSA-N

Molfile:  

 
     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   19.8355   -2.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0071   -1.3661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4198   -2.0760    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.8282   -1.3636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1880   -3.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868   -4.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8949   -4.9554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6046   -4.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6017   -3.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8931   -3.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3049   -3.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0144   -3.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7201   -3.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7174   -2.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0032   -2.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3005   -2.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1328   -2.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5482   -2.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5505   -3.2984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2548   -2.0707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9637   -2.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8312   -1.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5412   -1.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6703   -2.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3717   -1.6552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9659   -3.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6747   -3.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6769   -4.5184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3813   -3.2907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4802   -3.3184    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 11  1  0
 14  3  1  0
  3 17  1  0
 17  1  1  0
  1 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
  1 22  1  0
  1 23  1  0
 21 24  1  0
 24 25  3  0
 21 26  1  6
 26 27  1  0
 27 28  1  0
 27 29  2  0
  5 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538455

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 432.48

Molecular Weight (Monoisotopic): 432.1268

AlogP: 1.57

#Rotatable Bonds: 8

Polar Surface Area: 143.01

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.26

CX Basic pKa: 2.28

CX LogP: 0.42

CX LogD: 0.42

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -1.24

References

1. 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