(S,E)-ethyl 4-(2-(1-(2-acetamido-3-methylbut-2-enoyl)pyrrolidine-2-carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl)-4-oxobut-2-enoate

ID: ALA1950111

PubChem CID: 57391261

Max Phase: Preclinical

Molecular Formula: C20H29N5O7

Molecular Weight: 451.48

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(NC(C)=O)=C(C)C

Standard InChI:  InChI=1S/C20H29N5O7/c1-5-32-17(29)9-8-16(28)25(11-15(21)27)23-19(30)14-7-6-10-24(14)20(31)18(12(2)3)22-13(4)26/h8-9,14H,5-7,10-11H2,1-4H3,(H2,21,27)(H,22,26)(H,23,30)/b9-8+/t14-/m0/s1

Standard InChI Key:  DQFYLNZAQKRLTN-VFNNOXKTSA-N

Molfile:  

     RDKit          2D

 32 32  0  0  0  0  0  0  0  0999 V2000
    3.1375   -4.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125   -4.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0551   -3.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -3.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3901   -3.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3384   -3.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7263   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0124   -1.8281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3339   -2.3192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6262   -3.5606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0907   -3.1521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027   -3.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0727   -2.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -1.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7600   -1.0745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5013   -2.2962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7983   -4.3933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5194   -3.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317   -3.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484   -3.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606   -3.5838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3773   -3.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0895   -3.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9528   -2.3424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4414   -1.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4426   -1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1552   -2.2438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8703   -1.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5842   -2.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8716   -1.0074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1577   -0.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7288   -0.5917    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  2  0
 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
 26 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1950111

   ethyl (E)-4-[[[(2S)-1-(2-acetamido-3-methylbut-2-enoyl)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: 451.48

Molecular Weight (Monoisotopic): 451.2067

AlogP: -1.13

#Rotatable Bonds: 8

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: 10.35

CX Basic pKa: ┄

CX LogP: -2.02

CX LogD: -2.02

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.24

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