N-(tert-butoxycarbonyl)-phenylalanyl-sarcosine-nitrile

ID: ALA200743

PubChem CID: 11616689

Max Phase: Preclinical

Molecular Formula: C17H23N3O3

Molecular Weight: 317.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(CC#N)C(=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C

Standard InChI:  InChI=1S/C17H23N3O3/c1-17(2,3)23-16(22)19-14(15(21)20(4)11-10-18)12-13-8-6-5-7-9-13/h5-9,14H,11-12H2,1-4H3,(H,19,22)/t14-/m0/s1

Standard InChI Key:  KUTGRNFRYAFFRV-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  1  0  0  0  0  0999 V2000
   -3.3833  -11.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6689  -10.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544  -11.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6689   -9.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399  -10.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5254  -11.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1890  -10.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5254  -11.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035  -11.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6180  -10.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3360  -10.1949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833  -11.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3875  -12.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5583  -11.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083  -11.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399   -9.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1890   -9.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6583   -9.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1416   -9.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7229   -8.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5051   -8.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2993   -7.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8771   -8.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0
  1  2  1  0
 12 13  1  0
  6  7  1  0
 12 14  1  0
  2  4  2  0
 12 15  1  0
  6  8  2  0
  5 16  1  1
  7 17  1  0
  7  9  1  0
 16 18  1  0
  3  5  1  0
 18 19  2  0
  9 10  1  0
 19 20  1  0
  2  3  1  0
 20 21  2  0
 10 11  3  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA200743

   tert-butyl N-[(1S)-1-[(cyanomethyl)(methyl)carbamoyl]-2-phenylethyl]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: 317.39

Molecular Weight (Monoisotopic): 317.1739

AlogP: 2.10

#Rotatable Bonds: 5

Polar Surface Area: 82.43

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.36

CX Basic pKa: ┄

CX LogP: 1.75

CX LogD: 1.75

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -1.09

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. Schmitz J, Li T, Bartz U, Gütschow M..  (2016)  Cathepsin B Inhibitors: Combining Dipeptide Nitriles with an Occluding Loop Recognition Element by Click Chemistry.,  7  (3): [PMID:26985300] [10.1021/acsmedchemlett.5b00474]

Source

Source(1):

• Scientific Literature