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

ID: ALA101077

PubChem CID: 44332569

Max Phase: Preclinical

Molecular Formula: C19H33N5O5

Molecular Weight: 411.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)OCC(C)(C)C)C(=O)N[C@@H](C)C(=O)NCC(=O)NCC#N

Standard InChI:  InChI=1S/C19H33N5O5/c1-12(2)9-14(24-18(28)29-11-19(4,5)6)17(27)23-13(3)16(26)22-10-15(25)21-8-7-20/h12-14H,8-11H2,1-6H3,(H,21,25)(H,22,26)(H,23,27)(H,24,28)/t13-,14-/m0/s1

Standard InChI Key:  HTZCKWBGKSIZLQ-KBPBESRZSA-N

Molfile:  

     RDKit          2D

 29 28  0  0  1  0  0  0  0  0999 V2000
    4.0292   -3.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -3.2625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -3.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1667   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -3.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -3.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1875   -2.8625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -3.6750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -3.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4667   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3167   -3.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -4.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -2.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1667   -2.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1667   -3.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -2.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3167   -4.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6042   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0292   -3.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -3.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7417   -3.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -4.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2708   -4.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -1.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  9  1  0
  5  1  1  0
  6  5  1  0
  7 10  3  0
  8  4  1  0
  9  2  1  0
 10 22  1  0
 11 18  1  0
 12  1  2  0
 13  3  2  0
 14  4  2  0
 15  3  1  0
  5 16  1  1
 17 11  2  0
 18  8  1  0
 19 21  1  0
 20 11  1  0
 21 15  1  0
 22 20  1  0
 23 16  1  0
  9 24  1  6
 25 19  1  0
 26 19  1  0
 27 19  1  0
 28 23  1  0
 29 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA101077

   2,2-dimethylpropyl N-[(2S)-1-[[(2S)-1-[[2-(cyanomethylamino)-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: 411.50

Molecular Weight (Monoisotopic): 411.2482

AlogP: 0.43

#Rotatable Bonds: 10

Polar Surface Area: 149.42

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.59

CX Basic pKa: ┄

CX LogP: 0.05

CX LogD: 0.05

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -0.92

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