N-(tert-butoxycarbonyl)-2'-biphenylalanyl-glycine-nitrile

ID: ALA197498

PubChem CID: 11603305

Max Phase: Preclinical

Molecular Formula: C22H25N3O3

Molecular Weight: 379.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1-c1ccccc1)C(=O)NCC#N

Standard InChI:  InChI=1S/C22H25N3O3/c1-22(2,3)28-21(27)25-19(20(26)24-14-13-23)15-17-11-7-8-12-18(17)16-9-5-4-6-10-16/h4-12,19H,14-15H2,1-3H3,(H,24,26)(H,25,27)/t19-/m0/s1

Standard InChI Key:  UADNMMTUONBPLW-IBGZPJMESA-N

Molfile:  

     RDKit          2D

 28 29  0  0  1  0  0  0  0  0999 V2000
    9.9708  -16.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6853  -16.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3998  -16.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6853  -15.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1142  -16.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8287  -16.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5432  -16.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8287  -17.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2577  -16.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9721  -16.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6901  -15.7449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9708  -17.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9667  -18.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7958  -17.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1458  -17.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1142  -15.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8287  -14.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5430  -15.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2569  -14.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2574  -14.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5379  -13.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8268  -14.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1112  -13.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1100  -12.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3951  -12.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6809  -12.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6861  -13.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4016  -14.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  2  0
 12 15  1  0
  6  8  2  0
  5 16  1  1
 16 17  1  0
  7  9  1  0
 17 18  2  0
  3  5  1  0
 18 19  1  0
  9 10  1  0
 19 20  2  0
  2  3  1  0
 20 21  1  0
 10 11  3  0
 21 22  2  0
 22 17  1  0
  5  6  1  0
  1 12  1  0
 23 24  2  0
  1  2  1  0
 24 25  1  0
 12 13  1  0
 25 26  2  0
  6  7  1  0
 26 27  1  0
 12 14  1  0
 27 28  2  0
 28 23  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA197498

   tert-butyl N-[(1S)-1-[(cyanomethyl)carbamoyl]-2-(2-phenylphenyl)ethyl]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: 379.46

Molecular Weight (Monoisotopic): 379.1896

AlogP: 3.43

#Rotatable Bonds: 6

Polar Surface Area: 91.22

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.28

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.75

Np Likeness Score: -0.73

References

1. Löser R, Schilling K, Dimmig E, Gütschow M..  (2005)  Interaction of papain-like cysteine proteases with dipeptide-derived nitriles.,  48  (24): [PMID:16302809] [10.1021/jm050686b]

Source

Source(1):

• Scientific Literature