(S,E)-ethyl 4-(2-(1-acetylpyrrolidine-2-carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl)-4-oxobut-2-enoate

ID: ALA1950280

Cas Number: 1312616-49-1

PubChem CID: 57399677

Max Phase: Preclinical

Molecular Formula: C15H22N4O6

Molecular Weight: 354.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)/C=C/C(=O)N(CC(N)=O)NC(=O)[C@@H]1CCCN1C(C)=O

Standard InChI:  InChI=1S/C15H22N4O6/c1-3-25-14(23)7-6-13(22)19(9-12(16)21)17-15(24)11-5-4-8-18(11)10(2)20/h6-7,11H,3-5,8-9H2,1-2H3,(H2,16,21)(H,17,24)/b7-6+/t11-/m0/s1

Standard InChI Key:  QXSVKQKIGCAZOA-MLRMMBSGSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  1  0  0  0  0  0999 V2000
   12.3347   -6.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1414   -6.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2567   -5.2435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7644   -5.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2782   -6.4996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8797   -4.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3873   -4.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5026   -3.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9888   -2.0397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102   -3.2959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3994   -4.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9068   -4.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -5.9203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015   -3.8534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1255   -2.0835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332   -2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1470   -3.3397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.0323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332   -2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8264   -2.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1470   -3.3397    0.0000 C   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  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  2  0
 18 16  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1950280

   CID 57399677

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: 354.36

Molecular Weight (Monoisotopic): 354.1539

AlogP: -1.54

#Rotatable Bonds: 6

Polar Surface Area: 139.11

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.27

CX Basic pKa: ┄

CX LogP: -2.07

CX LogD: -2.07

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.34

Np Likeness Score: -0.59

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]

2.  (2016)  Specific inhibitors and active site probes for legumain, 

Source

Source(2):

• Scientific Literature
• BindingDB Database