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

ID: ALA102893

PubChem CID: 44332642

Max Phase: Preclinical

Molecular Formula: C21H31N5O6

Molecular Weight: 449.51

Molecule Type: Protein

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)=O

Standard InChI:  InChI=1S/C21H31N5O6/c1-13(2)9-16(26-21(31)32-12-15-7-5-4-6-8-15)20(30)25-14(3)19(29)24-11-18(28)23-10-17(22)27/h4-8,13-14,16H,9-12H2,1-3H3,(H2,22,27)(H,23,28)(H,24,29)(H,25,30)(H,26,31)/t14-,16-/m0/s1

Standard InChI Key:  SDYHTAPICGJMPG-HOCLYGCPSA-N

Molfile:  

     RDKit          2D

 32 32  0  0  1  0  0  0  0  0999 V2000
    3.9250   -7.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -7.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -7.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125   -7.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -7.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7875   -7.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -7.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2167   -7.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3625   -7.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9292   -7.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -8.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -6.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -6.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667   -7.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125   -6.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2125   -8.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3625   -6.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -7.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6417   -7.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0750   -7.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542   -7.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625   -7.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -5.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -8.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625   -8.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750   -7.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -5.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875   -7.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750   -8.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7958   -8.2875    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 10  1  0
 22 15  1  0
 23 22  1  0
 24 16  1  0
  8 25  1  6
 26 23  1  0
 27 23  2  0
 28 24  1  0
 29 24  1  0
 30 27  1  0
 31 26  2  0
 32 30  2  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA102893

   Cbz-Leu-Ala-Gly-Gly-NH2

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: 449.51

Molecular Weight (Monoisotopic): 449.2274

AlogP: -0.45

#Rotatable Bonds: 12

Polar Surface Area: 168.72

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.00

CX Basic pKa: ┄

CX LogP: -0.72

CX LogD: -0.72

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: -0.70

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