Benzyl N-[(1S)-1-benzyl-2-(2-cyanoethylamino)-2-oxo-ethyl]carbamate

ID: ALA4549686

PubChem CID: 155543483

Max Phase: Preclinical

Molecular Formula: C20H21N3O3

Molecular Weight: 351.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#CCCNC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C20H21N3O3/c21-12-7-13-22-19(24)18(14-16-8-3-1-4-9-16)23-20(25)26-15-17-10-5-2-6-11-17/h1-6,8-11,18H,7,13-15H2,(H,22,24)(H,23,25)/t18-/m0/s1

Standard InChI Key:  RRDFQSSXRRLDNP-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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   28.3169   -2.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0246   -2.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7323   -2.7240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4400   -2.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1477   -2.7240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4400   -1.4982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8555   -2.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5632   -2.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8555   -1.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5632   -3.5412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2709   -2.3154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9786   -2.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6863   -2.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3940   -2.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5632   -1.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2708   -1.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9780   -1.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9784   -0.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2657    0.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5614   -0.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6097   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9024   -2.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9020   -3.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6147   -3.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3190   -3.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1011   -3.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  1
  8 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  9 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  1 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25  1  1  0
 14 26  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4549686

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 351.41

Molecular Weight (Monoisotopic): 351.1583

AlogP: 2.55

#Rotatable Bonds: 8

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: 13.29

CX Basic pKa: ┄

CX LogP: 2.43

CX LogD: 2.43

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -0.68

References

1. Qiu Z, Kuhn B, Aebi J, Lin X, Ding H, Zhou Z, Xu Z, Xu D, Han L, Liu C, Qiu H, Zhang Y, Haap W, Riemer C, Stahl M, Qin N, Shen HC, Tang G..  (2016)  Discovery of Fluoromethylketone-Based Peptidomimetics as Covalent ATG4B (Autophagin-1) Inhibitors.,  7  (8): [PMID:27563406] [10.1021/acsmedchemlett.6b00208]

Source

Source(1):

• Scientific Literature