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

ID: ALA100227

PubChem CID: 10388030

Max Phase: Preclinical

Molecular Formula: C21H29N5O5

Molecular Weight: 431.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](C)C(=O)NCC(=O)NCC#N

Standard InChI:  InChI=1S/C21H29N5O5/c1-14(2)11-17(26-21(30)31-13-16-7-5-4-6-8-16)20(29)25-15(3)19(28)24-12-18(27)23-10-9-22/h4-8,14-15,17H,10-13H2,1-3H3,(H,23,27)(H,24,28)(H,25,29)(H,26,30)/t15-,17-/m0/s1

Standard InChI Key:  ROEVJNVNQYBLEQ-RDJZCZTQSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  1  0  0  0  0  0999 V2000
    4.3875   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -3.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -3.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -3.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -3.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5375   -2.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2500   -3.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8250   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6792   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875   -4.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -2.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375   -2.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -3.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6750   -4.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4000   -3.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167   -3.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1125   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -4.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125   -3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1875   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250   -3.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125   -4.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250   -4.3417    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 11  1  0
 20 15  1  0
 21 20  1  0
 22 19  1  0
 23 16  1  0
  9 24  1  6
 25 21  1  0
 26 21  2  0
 27 23  1  0
 28 23  1  0
 29 26  1  0
 30 25  2  0
 31 29  2  0
 31 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA100227

   benzyl 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: 431.49

Molecular Weight (Monoisotopic): 431.2169

AlogP: 0.59

#Rotatable Bonds: 11

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: 11.56

CX Basic pKa: ┄

CX LogP: 0.15

CX LogD: 0.15

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -0.86

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