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

ID: ALA1950273

PubChem CID: 57401385

Max Phase: Preclinical

Molecular Formula: C20H27N5O7

Molecular Weight: 449.46

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)/C=C/C(=O)OCC

Standard InChI:  InChI=1S/C20H27N5O7/c1-4-7-14(22-13(3)26)20(31)24-11-6-8-15(24)19(30)23-25(12-16(21)27)17(28)9-10-18(29)32-5-2/h1,9-10,14-15H,5-8,11-12H2,2-3H3,(H2,21,27)(H,22,26)(H,23,30)/b10-9+/t14-,15-/m0/s1

Standard InChI Key:  HOMCLOIEKNKVPL-CWCINCBISA-N

Molfile:  

     RDKit          2D

 32 32  0  0  0  0  0  0  0  0999 V2000
   15.9084   -8.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0834   -8.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8259   -8.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4959   -7.6875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1609   -8.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1092   -7.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4971   -6.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7833   -6.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1047   -6.9400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3970   -8.1814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6802   -7.7729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9681   -8.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6981   -6.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9928   -6.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0108   -5.6954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2695   -6.9170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9725   -9.0142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2514   -7.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5392   -8.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8225   -7.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1102   -8.2046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3936   -7.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6813   -8.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8180   -6.9633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2122   -6.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2135   -5.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9261   -6.8647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6412   -6.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3550   -6.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6424   -5.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9286   -5.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6437   -4.8033    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
 11 12  1  0
  7 25  1  0
  3  6  1  1
 25 26  1  6
 11 13  1  0
 25 27  1  0
 27 28  1  0
 13 14  1  0
 28 29  1  0
  4  7  1  0
 28 30  2  0
 14 15  2  0
 26 31  1  0
  2  3  1  0
 31 32  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA1950273

   ethyl (E)-4-[[[(2S)-1-[(2S)-2-acetamidopent-4-ynoyl]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: 449.46

Molecular Weight (Monoisotopic): 449.1910

AlogP: -2.03

#Rotatable Bonds: 9

Polar Surface Area: 168.21

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.25

CX Basic pKa: ┄

CX LogP: -2.45

CX LogD: -2.45

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.16

Np Likeness Score: -0.55

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