N-(tert-butoxycarbonyl)-azaphenylalanyl-glycine-nitrile

ID: ALA381659

PubChem CID: 11652420

Max Phase: Preclinical

Molecular Formula: C15H20N4O3

Molecular Weight: 304.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)NN(Cc1ccccc1)C(=O)NCC#N

Standard InChI:  InChI=1S/C15H20N4O3/c1-15(2,3)22-14(21)18-19(13(20)17-10-9-16)11-12-7-5-4-6-8-12/h4-8H,10-11H2,1-3H3,(H,17,20)(H,18,21)

Standard InChI Key:  ZBNPMOCJFPOVIC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    5.1708   -0.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8853   -0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5998   -0.9333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8853    0.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3142   -0.5208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0287   -0.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7432   -0.5208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0287   -1.7583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4577   -0.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1721   -0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8901   -0.1116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1708   -1.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3142    0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0287    0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7430    0.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4569    0.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4574    1.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7379    1.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0268    1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -2.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9958   -1.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3458   -1.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  1 12  1  0
  1  2  1  0
  5 13  1  0
  6  7  1  0
 13 14  1  0
  2  4  2  0
 14 15  2  0
  6  8  2  0
 15 16  1  0
 16 17  2  0
  7  9  1  0
 17 18  1  0
  3  5  1  0
 18 19  2  0
 19 14  1  0
  9 10  1  0
 12 20  1  0
  2  3  1  0
 12 21  1  0
 10 11  3  0
 12 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA381659

   Phenylalanine derivative, 48

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: 304.35

Molecular Weight (Monoisotopic): 304.1535

AlogP: 2.16

#Rotatable Bonds: 3

Polar Surface Area: 94.46

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.79

CX Basic pKa: ┄

CX LogP: 1.43

CX LogD: 1.43

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.66

Np Likeness Score: -1.02

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]

2. Schirmeister T, Schmitz J, Jung S, Schmenger T, Krauth-Siegel RL, Gütschow M..  (2017)  Evaluation of dipeptide nitriles as inhibitors of rhodesain, a major cysteine protease of Trypanosoma brucei.,  27  (1): [PMID:27890381] [10.1016/j.bmcl.2016.11.036]

Source

Source(1):

• Scientific Literature