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

ID: ALA1950112

PubChem CID: 57391262

Max Phase: Preclinical

Molecular Formula: C19H27N5O7

Molecular Weight: 437.45

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)C1(NC(C)=O)CC1

Standard InChI:  InChI=1S/C19H27N5O7/c1-3-31-16(28)7-6-15(27)24(11-14(20)26)22-17(29)13-5-4-10-23(13)18(30)19(8-9-19)21-12(2)25/h6-7,13H,3-5,8-11H2,1-2H3,(H2,20,26)(H,21,25)(H,22,29)/b7-6+/t13-/m0/s1

Standard InChI Key:  RSAAOECPPSSDMH-YBJDMEARSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   15.5417   -1.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9583   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3707   -1.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6584   -4.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8334   -4.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5759   -3.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2459   -3.2250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9109   -3.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8592   -3.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2471   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5333   -1.9864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8547   -2.4775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1470   -3.7189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4302   -3.3104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7181   -3.7267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4481   -2.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7428   -2.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7608   -1.2329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0195   -2.4545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7225   -4.5517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0014   -3.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2892   -3.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5725   -3.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8602   -3.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1436   -3.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4313   -3.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5680   -2.5008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6761   -2.4022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3912   -1.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1050   -2.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3924   -1.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 14 16  1  0
  8  4  1  0
 16 17  1  0
  1  3  1  0
 17 18  2  0
  6  9  1  1
 17 19  1  0
 15 20  2  0
  7 10  1  0
 15 21  1  0
  2  1  1  0
 21 22  2  0
 10 11  2  0
 22 23  1  0
  3  2  1  0
 23 24  1  0
  9 12  2  0
 24 25  1  0
  4  5  1  0
 25 26  1  0
  9 13  1  0
 23 27  2  0
 10  2  1  0
  5  6  1  0
  2 28  1  0
 13 14  1  0
 28 29  1  0
  6  7  1  0
 29 30  1  0
 14 15  1  0
 29 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1950112

   ethyl (E)-4-[[[(2S)-1-(1-acetamidocyclopropanecarbonyl)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: 437.45

Molecular Weight (Monoisotopic): 437.1910

AlogP: -1.89

#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: 10.26

CX Basic pKa: ┄

CX LogP: -2.48

CX LogD: -2.48

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.23

Np Likeness Score: -0.70

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