(S)-2-(2-azidoacetamido)-N-((S)-1-(cyanomethylamino)-1-oxo-3-phenylpropan-2-yl)-3-phenylpropanamide

ID: ALA3357963

PubChem CID: 118722556

Max Phase: Preclinical

Molecular Formula: C22H23N7O3

Molecular Weight: 433.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)CN=[N+]=[N-]

Standard InChI:  InChI=1S/C22H23N7O3/c23-11-12-25-21(31)18(13-16-7-3-1-4-8-16)28-22(32)19(27-20(30)15-26-29-24)14-17-9-5-2-6-10-17/h1-10,18-19H,12-15H2,(H,25,31)(H,27,30)(H,28,32)/t18-,19-/m0/s1

Standard InChI Key:  HXOHLJNPVFARRG-OALUTQOASA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    3.5985   -3.1801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0179   -2.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4357   -2.0258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1335   -3.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8412   -3.1862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1335   -4.4120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5489   -3.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2566   -3.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9643   -3.5948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2566   -2.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6720   -3.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5489   -4.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3797   -3.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0841   -4.0015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4293   -3.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7208   -3.5933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4311   -2.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1397   -1.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -3.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053   -3.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0157   -2.3660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2518   -4.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2533   -5.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9643   -6.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6741   -5.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6686   -4.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9571   -4.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8485   -2.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5566   -1.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5588   -1.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8470   -0.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1418   -1.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  4  5  1  0
  4  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
  7 12  1  6
 12 22  1  0
 11 13  1  0
 13 14  3  0
  4 15  1  0
 15 16  1  0
 15 17  1  1
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  2  0
 20  1  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 18 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 18  1  0
M  CHG  2   2   1   3  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3357963

   ---

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: 433.47

Molecular Weight (Monoisotopic): 433.1862

AlogP: 1.39

#Rotatable Bonds: 11

Polar Surface Area: 159.85

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -10.25

CX Basic pKa: ┄

CX LogP: 0.97

CX LogD: 0.86

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.21

Np Likeness Score: -0.33

References

1. Wammes AE, Hendriks TG, Amatdjais-Groenen HI, Wijdeven MA, van Hest JC, van Delft FL, Ritschel T, Rutjes FP..  (2014)  Influence of azide incorporation on binding affinity by small papain inhibitors.,  22  (20): [PMID:24972724] [10.1016/j.bmc.2014.06.001]

Source

Source(1):

• Scientific Literature