(S)-4'-(azidomethyl)-N-(1-(cyanomethylamino)-4-methyl-1-oxopentan-2-yl)biphenyl-4-carboxamide

ID: ALA3357958

PubChem CID: 118722551

Max Phase: Preclinical

Molecular Formula: C22H24N6O2

Molecular Weight: 404.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)c1ccc(-c2ccc(CN=[N+]=[N-])cc2)cc1)C(=O)NCC#N

Standard InChI:  InChI=1S/C22H24N6O2/c1-15(2)13-20(22(30)25-12-11-23)27-21(29)19-9-7-18(8-10-19)17-5-3-16(4-6-17)14-26-28-24/h3-10,15,20H,12-14H2,1-2H3,(H,25,30)(H,27,29)/t20-/m0/s1

Standard InChI Key:  VWEPMGHWYYIYNM-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    5.9696   -2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6773   -1.8903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9696   -3.1160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3850   -2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0927   -1.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8004   -2.2989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0927   -1.0731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5081   -1.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3850   -3.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2158   -2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9203   -2.7056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0896   -3.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7937   -3.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -1.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2668   -1.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5599   -0.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8512   -1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8539   -1.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5613   -2.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1430   -0.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479    0.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4410    0.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7324    0.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7350   -0.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4424   -1.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0261    0.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3225    0.1573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3894   -0.2512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1055   -0.6596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0895   -4.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  6  8  1  0
  4  9  1  6
  9 12  1  0
  8 10  1  0
 10 11  3  0
 13 12  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  1 14  1  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 27 26  1  0
 23 26  1  0
 27 28  2  0
 28 29  2  0
 12 30  1  0
M  CHG  2  28   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3357958

   ---

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: 404.47

Molecular Weight (Monoisotopic): 404.1961

AlogP: 3.95

#Rotatable Bonds: 9

Polar Surface Area: 130.75

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.02

CX Basic pKa: ┄

CX LogP: 3.00

CX LogD: 2.89

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: -0.57

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