{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionylamino]-acetylamino}-acetic acid methyl ester

ID: ALA319225

PubChem CID: 44332644

Max Phase: Preclinical

Molecular Formula: C22H32N4O7

Molecular Weight: 464.52

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H32N4O7/c1-14(2)10-17(26-22(31)33-13-16-8-6-5-7-9-16)21(30)25-15(3)20(29)24-11-18(27)23-12-19(28)32-4/h5-9,14-15,17H,10-13H2,1-4H3,(H,23,27)(H,24,29)(H,25,30)(H,26,31)/t15-,17-/m0/s1

Standard InChI Key:  FHXSQTSKUZXNKK-RDJZCZTQSA-N

Molfile:  

     RDKit          2D

 33 33  0  0  1  0  0  0  0  0999 V2000
    6.5917   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3125   -2.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7417   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -3.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4542   -3.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0292   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8875   -3.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0292   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6042   -2.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -3.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -1.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7417   -1.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375   -3.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8792   -3.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0292   -1.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1750   -2.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3167   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7417   -3.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0292   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4542   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042   -3.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3917   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -3.8667    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 15  1  0
 22 10  1  0
 23 21  1  0
 24 16  1  0
  8 25  1  6
 26 22  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:

   

   ALA319225

   Cbz-Leu-Ala-Gly-Gly-OMe

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 464.52

Molecular Weight (Monoisotopic): 464.2271

AlogP: 0.24

#Rotatable Bonds: 12

Polar Surface Area: 151.93

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.83

CX Basic pKa: ┄

CX LogP: 0.24

CX LogD: 0.24

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.32

Np Likeness Score: -0.58

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