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

ID: ALA1950282

PubChem CID: 57398022

Max Phase: Preclinical

Molecular Formula: C19H29N5O8

Molecular Weight: 455.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H29N5O8/c1-4-11(21-10(3)25)17(28)23-8-6-7-12(23)16(27)22-24(9-13(20)26)18(29)14-15(32-14)19(30)31-5-2/h11-12,14-15H,4-9H2,1-3H3,(H2,20,26)(H,21,25)(H,22,27)/t11-,12-,14?,15?/m0/s1

Standard InChI Key:  RKUQFNRGTWIVKQ-XOEAPDPESA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   14.9792  -26.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8042  -26.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0616  -25.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3917  -25.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7266  -25.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7783  -25.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3904  -24.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1043  -24.1989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7828  -24.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4905  -25.9314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2074  -25.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9194  -25.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1894  -24.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8947  -24.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8768  -23.4454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6180  -24.6670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9150  -26.7642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0651  -25.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7773  -25.9546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4940  -25.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2062  -25.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0695  -24.7133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6753  -24.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3484  -25.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6380  -25.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3500  -25.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6741  -23.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9590  -22.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9615  -24.6147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2464  -24.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5325  -24.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2451  -23.3783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 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
 27 28  1  0
 13 14  1  0
 23 29  1  1
  4  7  1  0
 29 30  1  0
 14 15  1  0
 30 31  1  0
  2  3  1  0
 30 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1950282

   ethyl 3-[[[(2S)-1-[(2S)-2-acetamidobutanoyl]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: 455.47

Molecular Weight (Monoisotopic): 455.2016

AlogP: -2.43

#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: 10.18

CX Basic pKa: ┄

CX LogP: -2.94

CX LogD: -2.94

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.19

Np Likeness Score: -0.45

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