(E)-ethyl 4-(2-((S)-1-(-2-acetamidobut-2-enoyl)pyrrolidine-2-carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl)-4-oxobut-2-enoate

ID: ALA1950110

PubChem CID: 57391260

Max Phase: Preclinical

Molecular Formula: C19H27N5O7

Molecular Weight: 437.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C(\NC(C)=O)C(=O)N1CCC[C@H]1C(=O)NN(CC(N)=O)C(=O)/C=C/C(=O)OCC

Standard InChI:  InChI=1S/C19H27N5O7/c1-4-13(21-12(3)25)19(30)23-10-6-7-14(23)18(29)22-24(11-15(20)26)16(27)8-9-17(28)31-5-2/h4,8-9,14H,5-7,10-11H2,1-3H3,(H2,20,26)(H,21,25)(H,22,29)/b9-8+,13-4-/t14-/m0/s1

Standard InChI Key:  ZXRAADWJDYNJKC-IWKCOGPUSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   16.4042   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5792   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3218    0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9917    0.9708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6567    0.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6051    0.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9930    1.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2791    2.2094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6006    1.7183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8928    0.4769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1760    0.8854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4639    0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1940    1.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4887    2.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5066    2.9630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7654    1.7413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4684   -0.3558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7472    0.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0350    0.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3183    0.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6061    0.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8894    0.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1772    0.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139    1.6951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7081    2.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7093    3.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4219    1.7937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1370    2.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8508    1.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1383    3.0301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4244    3.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 14 16  1  0
  7  8  2  0
 12 17  2  0
  3  4  1  0
 12 18  1  0
  6  9  2  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  6 10  1  0
 20 21  1  0
  5  1  1  0
 21 22  1  0
 10 11  1  0
 22 23  1  0
  1  2  1  0
 20 24  2  0
 11 12  1  0
  7 25  1  0
  3  6  1  1
 25 26  2  0
 11 13  1  0
 25 27  1  0
 27 28  1  0
 13 14  1  0
 28 29  1  0
  4  7  1  0
 28 30  2  0
 14 15  2  0
 26 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1950110

   ethyl (E)-4-[[[(2S)-1-[(Z)-2-acetamidobut-2-enoyl]pyrrolidine-2-carbonyl]amino]-(2-amino-2-oxoethyl)amino]-4-oxobut-2-enoate

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: 437.45

Molecular Weight (Monoisotopic): 437.1910

AlogP: -1.52

#Rotatable Bonds: 8

Polar Surface Area: 168.21

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.31

CX Basic pKa: ┄

CX LogP: -2.26

CX LogD: -2.26

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.24

Np Likeness Score: -0.58

References

1. Lee J, Bogyo M..  (2012)  Synthesis and evaluation of aza-peptidyl inhibitors of the lysosomal asparaginyl endopeptidase, legumain.,  22  (3): [PMID:22243962] [10.1016/j.bmcl.2011.12.079]

Source

Source(1):

• Scientific Literature