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

ID: ALA1950274

PubChem CID: 57396165

Max Phase: Preclinical

Molecular Formula: C21H31N5O7

Molecular Weight: 465.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)/C=C/C(=O)N(CC(N)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1CCCCN1C(C)=O

Standard InChI:  InChI=1S/C21H31N5O7/c1-3-33-19(30)10-9-18(29)26(13-17(22)28)23-20(31)15-8-6-12-25(15)21(32)16-7-4-5-11-24(16)14(2)27/h9-10,15-16H,3-8,11-13H2,1-2H3,(H2,22,28)(H,23,31)/b10-9+/t15-,16+/m0/s1

Standard InChI Key:  PTTXSDQOULKCCJ-DMGQIGSTSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
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    2.4242   -2.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668   -1.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8367   -0.9876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5017   -1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8380   -0.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1241    0.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4456   -0.2402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7378   -1.4815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0210   -1.0731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6911   -1.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390   -0.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6663    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6484    1.0045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3896   -0.2171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1200   -1.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8367   -1.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5489   -1.5047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2656   -1.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9778   -1.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8411   -0.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5543    1.0738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5488    0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2556   -0.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9723    0.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778    1.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2665    1.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416    1.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8452    2.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1254    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 26  7  1  6
 26 25  1  0
 11 12  1  0
  3  6  1  1
 11 13  1  0
 13 14  1  0
  4  7  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 14 15  2  0
  2  3  1  0
 14 16  1  0
 25 31  1  0
 31 32  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1950274

   ethyl (E)-4-[[[(2S)-1-[(2R)-1-acetylpiperidine-2-carbonyl]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: 465.51

Molecular Weight (Monoisotopic): 465.2223

AlogP: -1.16

#Rotatable Bonds: 7

Polar Surface Area: 159.42

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.34

CX Basic pKa: ┄

CX LogP: -1.89

CX LogD: -1.89

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.27

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]

Source

Source(1):

• Scientific Literature