2-(3-(2-Methoxyethyl)indolizin-1-yl)-2-oxo-N-(4-(trifluoromethoxy)phenyl)acetamide

ID: ALA3747282

PubChem CID: 127042237

Max Phase: Preclinical

Molecular Formula: C20H17F3N2O4

Molecular Weight: 406.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCc1cc(C(=O)C(=O)Nc2ccc(OC(F)(F)F)cc2)c2ccccn12

Standard InChI:  InChI=1S/C20H17F3N2O4/c1-28-11-9-14-12-16(17-4-2-3-10-25(14)17)18(26)19(27)24-13-5-7-15(8-6-13)29-20(21,22)23/h2-8,10,12H,9,11H2,1H3,(H,24,27)

Standard InChI Key:  SWSVOFPZAAGMJN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3808    3.5211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4505    2.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1182    4.3614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5870    4.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0571    6.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5257    6.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5244    5.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0544    3.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5858    3.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9944    5.5827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9920    4.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -4.3539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3028   -4.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1674    4.7032    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.6141    3.3225    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.7892    3.5645    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  2  0
 11 14  1  0
 14 15  1  0
  7 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 15  1  0
 20 23  1  0
 23 24  1  0
 17 25  1  0
 25 26  1  0
 24 27  1  0
 24 28  1  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3747282

   ---

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: 406.36

Molecular Weight (Monoisotopic): 406.1140

AlogP: 3.85

#Rotatable Bonds: 7

Polar Surface Area: 69.04

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.75

CX Basic pKa: ┄

CX LogP: 3.85

CX LogD: 3.85

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: -1.22

References

1. Colley HE, Muthana M, Danson SJ, Jackson LV, Brett ML, Harrison J, Coole SF, Mason DP, Jennings LR, Wong M, Tulasi V, Norman D, Lockey PM, Williams L, Dossetter AG, Griffen EJ, Thompson MJ..  (2015)  An Orally Bioavailable, Indole-3-glyoxylamide Based Series of Tubulin Polymerization Inhibitors Showing Tumor Growth Inhibition in a Mouse Xenograft Model of Head and Neck Cancer.,  58  (23): [PMID:26580420] [10.1021/acs.jmedchem.5b01312]

Source

Source(1):

• Scientific Literature