(S)-2-(2-azidoacetamido)-N-((S)-1-(cyanomethylamino)-1-oxo-3-phenylpropan-2-yl)-4-methylpentanamide

ID: ALA3357962

PubChem CID: 118722555

Max Phase: Preclinical

Molecular Formula: C19H25N7O3

Molecular Weight: 399.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H25N7O3/c1-13(2)10-15(24-17(27)12-23-26-21)19(29)25-16(18(28)22-9-8-20)11-14-6-4-3-5-7-14/h3-7,13,15-16H,9-12H2,1-2H3,(H,22,28)(H,24,27)(H,25,29)/t15-,16-/m0/s1

Standard InChI Key:  UGKZDTFZAABPED-HOTGVXAUSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
    2.6823   -2.6890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1017   -2.1131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5194   -1.5347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2172   -3.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9249   -2.6951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2172   -3.9209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6326   -3.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3404   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0481   -3.1037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3404   -1.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7558   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6326   -3.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4635   -3.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1679   -3.5104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5131   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8045   -3.1022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5149   -1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2235   -1.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2252   -0.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9303   -1.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0977   -2.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3891   -3.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0995   -1.8749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3356   -4.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3371   -5.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0480   -5.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7579   -5.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7523   -4.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0409   -3.9132    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 24  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
 18 19  1  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 21 23  2  0
 22  1  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  CHG  2   2   1   3  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3357962

   ---

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: 399.46

Molecular Weight (Monoisotopic): 399.2019

AlogP: 1.19

#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: 0.57

CX LogD: 0.46

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.22

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