(S)-N-(3-amino-1-cyano-3-oxopropyl)-3-((4-(6-methylpyridine-3-yl)phenyl)sulphonyl)-2,2-dimethylpropanamide

ID: ALA4549915

PubChem CID: 155550525

Max Phase: Preclinical

Molecular Formula: C21H24N4O4S

Molecular Weight: 428.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2ccc(S(=O)(=O)CC(C)(C)C(=O)N[C@H](C#N)CC(N)=O)cc2)cn1

Standard InChI:  InChI=1S/C21H24N4O4S/c1-14-4-5-16(12-24-14)15-6-8-18(9-7-15)30(28,29)13-21(2,3)20(27)25-17(11-22)10-19(23)26/h4-9,12,17H,10,13H2,1-3H3,(H2,23,26)(H,25,27)/t17-/m0/s1

Standard InChI Key:  ZJIFKWPSDDYXNO-KRWDZBQOSA-N

Molfile:  

 
     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   31.9159   -9.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0875   -9.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5002   -9.7114    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.9086   -8.9990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2684  -11.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2672  -12.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9753  -12.5907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6850  -12.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6821  -11.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9735  -10.9534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3853  -10.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0948  -11.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8005  -10.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7978  -10.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0836   -9.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3809  -10.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2132  -10.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6286  -10.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6309  -10.9338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3352   -9.7060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0441  -10.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9116   -8.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6216   -9.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7507   -9.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4521   -9.2906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0463  -10.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7551  -11.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7573  -12.1537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4617  -10.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5592  -12.5898    0.0000 C   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
  6 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4549915

   ---

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: 428.51

Molecular Weight (Monoisotopic): 428.1518

AlogP: 1.74

#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: 11.31

CX Basic pKa: 5.36

CX LogP: 0.41

CX LogD: 0.41

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.66

Np Likeness Score: -1.09

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