US9018255, 8a

ID: ALA3703581

PubChem CID: 56961830

Max Phase: Preclinical

Molecular Formula: C20H15F6NO3

Molecular Weight: 431.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(COC(=O)c1c(C(F)(F)F)cccc1C(F)(F)F)C(=O)NCc1ccccc1

Standard InChI:  InChI=1S/C20H15F6NO3/c1-12(17(28)27-10-13-6-3-2-4-7-13)11-30-18(29)16-14(19(21,22)23)8-5-9-15(16)20(24,25)26/h2-9H,1,10-11H2,(H,27,28)

Standard InChI Key:  YVRPNJWMIOZDRD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    3.6384   -0.9011    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984   -2.7004    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6377   -2.1009    0.0000 F   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
   -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
    0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0351   -3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -3.7494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078   -5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460   -5.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6109   -7.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5727   -8.1014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9117   -8.2481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9148   -9.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2157  -10.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2209  -11.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5226  -12.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8190  -11.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8138  -10.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5122   -9.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6384   -0.9011    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984   -2.7004    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6377   -2.1009    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  9 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3703581

   2-(Benzylcarbamoyl)prop-2-enyl 2,6-bis(trifluoromethyl)benzoate

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: 431.33

Molecular Weight (Monoisotopic): 431.0956

AlogP: 4.75

#Rotatable Bonds: 6

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.24

CX Basic pKa: ┄

CX LogP: 5.04

CX LogD: 5.04

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.41

Np Likeness Score: -0.72

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