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

ID: ALA101197

PubChem CID: 44332640

Max Phase: Preclinical

Molecular Formula: C23H34N4O7

Molecular Weight: 478.55

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H34N4O7/c1-5-33-20(29)13-24-19(28)12-25-21(30)16(4)26-22(31)18(11-15(2)3)27-23(32)34-14-17-9-7-6-8-10-17/h6-10,15-16,18H,5,11-14H2,1-4H3,(H,24,28)(H,25,30)(H,26,31)(H,27,32)/t16-,18-/m0/s1

Standard InChI Key:  AUOPJDONCZTWFS-WMZOPIPTSA-N

Molfile:  

     RDKit          2D

 34 34  0  0  1  0  0  0  0  0999 V2000
    3.1292   -7.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -7.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -7.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -7.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -7.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -7.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -7.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625   -7.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -7.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5667   -7.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1375   -7.3792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -8.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -6.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -6.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -7.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -6.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -8.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5667   -6.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -7.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8500   -7.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458   -7.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2792   -7.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583   -7.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -6.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625   -8.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9917   -7.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -7.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583   -8.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -5.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7042   -7.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -7.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -8.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5875   -8.5667    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 26  1  0
 32 27  1  0
 33 28  2  0
 34 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA101197

   Cbz-Leu-Ala-Gly-Gly-OEt

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: 478.55

Molecular Weight (Monoisotopic): 478.2427

AlogP: 0.63

#Rotatable Bonds: 13

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: 11.86

CX Basic pKa: ┄

CX LogP: 0.59

CX LogD: 0.59

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.30

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