trans-ethyl 3-(2-((S)-1-((S)-2-acetamidopent-4-ynoyl)pyrrolidine-2-carbonyl)-1-(2-amino-2-oxoethyl)hydrazinecarbonyl)oxirane-2-carboxylate

ID: ALA1950284

PubChem CID: 57396227

Max Phase: Preclinical

Molecular Formula: C20H27N5O8

Molecular Weight: 465.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CC[C@H](NC(C)=O)C(=O)N1CCC[C@H]1C(=O)NN(CC(N)=O)C(=O)C1OC1C(=O)OCC

Standard InChI:  InChI=1S/C20H27N5O8/c1-4-7-12(22-11(3)26)18(29)24-9-6-8-13(24)17(28)23-25(10-14(21)27)19(30)15-16(33-15)20(31)32-5-2/h1,12-13,15-16H,5-10H2,2-3H3,(H2,21,27)(H,22,26)(H,23,28)/t12-,13-,15?,16?/m0/s1

Standard InChI Key:  CASFIZWKQFXGOY-VRLRAXNCSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
   12.5917   -0.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4167   -0.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6741   -0.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0042    0.3083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3391   -0.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3908    0.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0029    1.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7168    1.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3953    1.0558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1030   -0.1856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8199    0.2229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5319   -0.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8019    1.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5072    1.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4893    2.3004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2305    1.0788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5275   -1.0184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6776    0.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3898   -0.2088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1065    0.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8187   -0.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6820    1.0325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2878    1.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9609   -0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2505    0.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9625    0.6291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2866    2.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5740    1.1311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8589    1.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1450    1.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8576    2.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0004    2.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7143    3.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
 12 17  2  0
 25 12  1  0
  3  4  1  0
 24 18  1  0
  6  9  2  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  6 10  1  0
 20 21  1  0
  5  1  1  0
 18 22  2  0
 10 11  1  0
 23  7  1  0
 25 24  1  0
  1  2  1  0
 11 12  1  0
  3  6  1  6
 25 26  1  0
 24 26  1  0
 11 13  1  0
 23 27  1  0
 13 14  1  0
 23 28  1  1
  4  7  1  0
 28 29  1  0
 14 15  1  0
 29 30  1  0
  2  3  1  0
 29 31  2  0
 27 32  1  0
 14 16  2  0
 32 33  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA1950284

   ethyl 3-[[[(2S)-1-[(2S)-2-acetamidopent-4-ynoyl]pyrrolidine-2-carbonyl]amino]-(2-amino-2-oxoethyl)carbamoyl]oxirane-2-carboxylate

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: 465.46

Molecular Weight (Monoisotopic): 465.1860

AlogP: -2.82

#Rotatable Bonds: 9

Polar Surface Area: 180.74

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.11

CX Basic pKa: ┄

CX LogP: -3.31

CX LogD: -3.31

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.14

Np Likeness Score: -0.51

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