[(S)-3-Methyl-1-((S)-1-{[(methylcarbamoylmethyl-carbamoyl)-methyl]-carbamoyl}-ethylcarbamoyl)-butyl]-carbamic acid benzyl ester

ID: ALA316577

PubChem CID: 44332690

Max Phase: Preclinical

Molecular Formula: C22H33N5O6

Molecular Weight: 463.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)CNC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C22H33N5O6/c1-14(2)10-17(27-22(32)33-13-16-8-6-5-7-9-16)21(31)26-15(3)20(30)25-12-19(29)24-11-18(28)23-4/h5-9,14-15,17H,10-13H2,1-4H3,(H,23,28)(H,24,29)(H,25,30)(H,26,31)(H,27,32)/t15-,17-/m0/s1

Standard InChI Key:  RMHCDPIPCYUWIK-RDJZCZTQSA-N

Molfile:  

     RDKit          2D

 33 33  0  0  1  0  0  0  0  0999 V2000
    3.9250   -7.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -7.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -7.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125   -7.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -7.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7875   -7.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -7.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2167   -7.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3625   -7.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9292   -7.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -8.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -6.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -6.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667   -7.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125   -6.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2125   -8.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3625   -6.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -7.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6417   -7.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0750   -7.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542   -7.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625   -7.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -5.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -8.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2875   -8.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750   -7.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625   -8.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -5.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750   -8.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875   -7.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7958   -8.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  8  1  0
  5  1  1  0
  6  5  1  0
  7  4  1  0
  8  2  1  0
  9 19  1  0
 10 20  1  0
 11  9  1  0
 12  1  2  0
 13  3  2  0
 14  4  2  0
 15  3  1  0
  5 16  1  1
 17  9  2  0
 18 10  2  0
 19  7  1  0
 20 11  1  0
 21 10  1  0
 22 15  1  0
 23 22  1  0
 24 16  1  0
  8 25  1  6
 26 21  1  0
 27 23  2  0
 28 23  1  0
 29 24  1  0
 30 24  1  0
 31 28  2  0
 32 27  1  0
 33 31  1  0
 32 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA316577

   Cbz-Leu-Ala-Gly-Gly-NHMe

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: 463.54

Molecular Weight (Monoisotopic): 463.2431

AlogP: -0.19

#Rotatable Bonds: 12

Polar Surface Area: 154.73

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.00

CX Basic pKa: ┄

CX LogP: -0.49

CX LogD: -0.49

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.29

Np Likeness Score: -0.64

References

1. Cornish JA, Murray H, Kemp GD, Gani D.  (1995)  Inhibitors of the adenovirus type 2 proteinase based on substrate-like tetrapeptide nitriles,  5  (1): [10.1016/0960-894X(94)00452-L]

Source

Source(1):

• Scientific Literature