(S)-4-(azidomethyl)-N-(1-(cyanomethylamino)-4-(4-hydroxyphenyl)-1-oxobutan-2-yl)benzamide

ID: ALA3357957

PubChem CID: 118722550

Max Phase: Preclinical

Molecular Formula: C20H20N6O3

Molecular Weight: 392.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCNC(=O)[C@H](CCc1ccc(O)cc1)NC(=O)c1ccc(CN=[N+]=[N-])cc1

Standard InChI:  InChI=1S/C20H20N6O3/c21-11-12-23-20(29)18(10-5-14-3-8-17(27)9-4-14)25-19(28)16-6-1-15(2-7-16)13-24-26-22/h1-4,6-9,18,27H,5,10,12-13H2,(H,23,29)(H,25,28)/t18-/m0/s1

Standard InChI Key:  BDOILNKOSNNEMJ-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   16.8597   -2.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5674   -1.9439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1520   -1.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8597   -3.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2751   -2.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9829   -1.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6906   -2.3525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9829   -1.1267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3983   -1.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2751   -3.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1060   -2.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8104   -2.7592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1569   -1.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4501   -0.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7414   -1.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7440   -1.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4515   -2.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0351   -0.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3315   -1.1231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6225   -1.5306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9106   -1.9390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9797   -3.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9784   -4.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2670   -4.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2653   -5.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9738   -6.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6855   -5.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6837   -4.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9736   -6.8468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  7  9  1  0
  5 10  1  6
 10 22  1  0
  9 11  1  0
 11 12  3  0
  3 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  3  1  0
 19 18  1  0
 15 18  1  0
 19 20  2  0
 20 21  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
M  CHG  2  20   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3357957

   ---

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: 392.42

Molecular Weight (Monoisotopic): 392.1597

AlogP: 2.57

#Rotatable Bonds: 9

Polar Surface Area: 150.98

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.50

CX Basic pKa: ┄

CX LogP: 1.90

CX LogD: 1.78

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.26

Np Likeness Score: -0.30

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