(S)-N-(3-amino-1-cyano-3-oxopropyl)-3-(4-(6-tert-butylpyridin-3-yl)phenylsulfonyl)-2,2-dimethylpropanamide

ID: ALA4547118

PubChem CID: 155552502

Max Phase: Preclinical

Molecular Formula: C24H30N4O4S

Molecular Weight: 470.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(CS(=O)(=O)c1ccc(-c2ccc(C(C)(C)C)nc2)cc1)C(=O)N[C@H](C#N)CC(N)=O

Standard InChI:  InChI=1S/C24H30N4O4S/c1-23(2,3)20-11-8-17(14-27-20)16-6-9-19(10-7-16)33(31,32)15-24(4,5)22(30)28-18(13-25)12-21(26)29/h6-11,14,18H,12,15H2,1-5H3,(H2,26,29)(H,28,30)/t18-/m0/s1

Standard InChI Key:  XKEUBOPSBXBIEK-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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   27.3759  -25.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5475  -24.6354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9603  -25.3453    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.3687  -24.6329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7284  -26.9962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   22.4353  -28.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1450  -27.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1422  -26.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4336  -26.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   25.2579  -25.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5437  -25.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.6733  -25.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0887  -25.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0909  -26.5677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7953  -25.3400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5041  -25.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3717  -24.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0817  -24.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2107  -25.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9122  -24.9245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5063  -26.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2152  -26.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2174  -27.7877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9218  -26.5600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0193  -28.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3119  -27.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0186  -29.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3060  -28.6265    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
 30 31  1  0
 30 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4547118

   ---

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: 470.60

Molecular Weight (Monoisotopic): 470.1988

AlogP: 2.73

#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: 4.83

CX LogP: 2.21

CX LogD: 2.21

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.61

Np Likeness Score: -1.05

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