US9018255, 3b

ID: ALA3703580

PubChem CID: 56945840

Max Phase: Preclinical

Molecular Formula: C21H26Cl2N2O6

Molecular Weight: 473.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(COC(=O)c1c(Cl)cccc1Cl)C(=O)NC(CC(C)C)C(=O)NCC(=O)OCC

Standard InChI:  InChI=1S/C21H26Cl2N2O6/c1-5-30-17(26)10-24-20(28)16(9-12(2)3)25-19(27)13(4)11-31-21(29)18-14(22)7-6-8-15(18)23/h6-8,12,16H,4-5,9-11H2,1-3H3,(H,24,28)(H,25,27)

Standard InChI Key:  ZQEFBSNKAVWNJR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   10.3720  -16.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3737  -15.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0755  -14.2734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0776  -12.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1179  -12.1744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7794  -12.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815  -10.5187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4833   -9.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4431  -10.3638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7850   -7.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7855   -6.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8245   -5.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7462   -5.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2297   -5.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -5.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 24  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3703580

   2-[[1-[(2-Ethoxy-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]prop-2-enyl 2,6-dichlorobenzoate

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: 473.35

Molecular Weight (Monoisotopic): 472.1168

AlogP: 2.92

#Rotatable Bonds: 11

Polar Surface Area: 110.80

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.97

CX Basic pKa: ┄

CX LogP: 3.47

CX LogD: 3.47

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -0.57

References

1.  (2015)  Esters of (acyloxymethyl)acrylamide, a pharmaceutical composition containing them, and their use as inhibitors of the thioredoxin‚Äîthioredoxin reductase system, 

Source

Source(1):

• BindingDB Database