(E)-ethyl 4-(2-((S)-1-((S)-3-acetylthiazolidine-4-carbonyl)pyrrolidine-2-carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl)-4-oxobut-2-enoate

ID: ALA1950275

PubChem CID: 57390946

Max Phase: Preclinical

Molecular Formula: C19H27N5O7S

Molecular Weight: 469.52

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]1CSCN1C(C)=O

Standard InChI:  InChI=1S/C19H27N5O7S/c1-3-31-17(28)7-6-16(27)24(9-15(20)26)21-18(29)13-5-4-8-22(13)19(30)14-10-32-11-23(14)12(2)25/h6-7,13-14H,3-5,8-11H2,1-2H3,(H2,20,26)(H,21,29)/b7-6+/t13-,14+/m0/s1

Standard InChI Key:  FNXYDKNQGXQKOH-HYLRALAJSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
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   15.0542  -13.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7968  -12.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.4680  -11.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7541  -10.6364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0756  -11.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3678  -12.3689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6510  -11.9604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9389  -12.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.9816   -9.8829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.9434  -13.2017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2222  -11.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5100  -12.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7933  -11.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0811  -12.3921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3644  -11.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6522  -12.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7889  -11.1508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1855   -9.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1788  -10.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9613  -10.8987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4516  -10.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9721   -9.5640    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.2098  -11.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6528  -12.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0154  -11.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 16  1  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  1
 26 25  1  0
 11 12  1  0
  3  6  1  1
 11 13  1  0
 13 14  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 25  1  0
  4  7  1  0
 27 30  1  0
 14 15  2  0
 30 31  2  0
  2  3  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1950275

   ethyl (E)-4-[[[(2S)-1-[(4S)-3-acetyl-1,3-thiazolidine-4-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: 469.52

Molecular Weight (Monoisotopic): 469.1631

AlogP: -1.64

#Rotatable Bonds: 7

Polar Surface Area: 159.42

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.23

CX Basic pKa: ┄

CX LogP: -2.47

CX LogD: -2.47

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.26

Np Likeness Score: -0.79

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