[(S)-1-((S)-1-{[(2,2-Dimethoxy-ethylcarbamoyl)-methyl]-carbamoyl}-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester

ID: ALA100630

PubChem CID: 44332583

Max Phase: Preclinical

Molecular Formula: C20H38N4O7

Molecular Weight: 446.55

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H38N4O7/c1-12(2)9-14(24-19(28)31-20(4,5)6)18(27)23-13(3)17(26)22-10-15(25)21-11-16(29-7)30-8/h12-14,16H,9-11H2,1-8H3,(H,21,25)(H,22,26)(H,23,27)(H,24,28)/t13-,14-/m0/s1

Standard InChI Key:  PNESGNHHMRVOFW-KBPBESRZSA-N

Molfile:  

     RDKit          2D

 31 30  0  0  1  0  0  0  0  0999 V2000
    3.1917   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9125   -0.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -1.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -1.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4875   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3375   -1.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -0.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2042   -0.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -2.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -0.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -2.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7750   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6292   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9167   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3417   -1.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6292   -0.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000    0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708   -1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3500    0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0625   -0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042    1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917    0.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  6  1  0
  5  8  1  0
  6  1  1  0
  7  5  1  0
  8  3  1  0
  9 18  1  0
 10  2  1  0
 11  2  2  0
 12  9  1  0
 13  1  2  0
 14  5  2  0
  6 15  1  1
 16  9  2  0
 17 10  1  0
 18  7  1  0
 19 20  1  0
 20 12  1  0
 21 19  1  0
 22 19  1  0
 23 15  1  0
  8 24  1  6
 25 17  1  0
 26 17  1  0
 27 17  1  0
 28 22  1  0
 29 21  1  0
 30 23  1  0
 31 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA100630

   tert-butyl N-[(2S)-1-[[(2S)-1-[[2-(2,2-dimethoxyethylamino)-2-oxoethyl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate

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: 446.55

Molecular Weight (Monoisotopic): 446.2740

AlogP: 0.28

#Rotatable Bonds: 12

Polar Surface Area: 144.09

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.08

CX Basic pKa: ┄

CX LogP: 0.17

CX LogD: 0.17

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.32

Np Likeness Score: -0.67

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