Trans-ethyl 3-(2-((S)-1-acetylpyrrolidine-2-carbonyl)-1-(2-amino-2-oxoethyl)hydrazinecarbonyl)oxirane-2-carboxylate

ID: ALA1950281

PubChem CID: 57401438

Max Phase: Preclinical

Molecular Formula: C15H22N4O7

Molecular Weight: 370.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1OC1C(=O)N(CC(N)=O)NC(=O)[C@@H]1CCCN1C(C)=O

Standard InChI:  InChI=1S/C15H22N4O7/c1-3-25-15(24)12-11(26-12)14(23)19(7-10(16)21)17-13(22)9-5-4-6-18(9)8(2)20/h9,11-12H,3-7H2,1-2H3,(H2,16,21)(H,17,22)/t9-,11?,12?/m0/s1

Standard InChI Key:  TZKVALJHLJILLI-GCVQQVDUSA-N

Molfile:  

     RDKit          2D

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    4.1791  -26.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041  -26.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2616  -25.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5916  -25.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9266  -25.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9783  -25.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5904  -24.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042  -23.9447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9828  -24.4359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6905  -25.6772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4073  -25.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1194  -25.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3894  -24.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0947  -24.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0767  -23.1912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8180  -24.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1150  -26.5100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2650  -25.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9773  -25.7004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6939  -25.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4062  -25.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2695  -24.4591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8753  -23.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5483  -25.6927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8380  -25.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500  -24.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 13  1  0
 13 14  1  0
  4  7  1  0
 14 15  1  0
  2  3  1  0
 14 16  2  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
  7 23  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
M  END

Alternative Forms

1. Parent:

   

   ALA1950281

   ethyl 3-[[[(2S)-1-acetylpyrrolidine-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: 370.36

Molecular Weight (Monoisotopic): 370.1488

AlogP: -2.33

#Rotatable Bonds: 6

Polar Surface Area: 151.64

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.11

CX Basic pKa: ┄

CX LogP: -2.93

CX LogD: -2.93

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.30

Np Likeness Score: -0.54

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