(E)-N-(4-(3-(2-Ethyl-2-propylhydrazinyl)-3-oxoprop-1-en-1-yl)benzyl)-2-(2-methyl-1H-indol-3-yl)ethanaminium 2,2,2-Trifluoroacetate

ID: ALA4475018

PubChem CID: 155537405

Max Phase: Preclinical

Molecular Formula: C28H35F3N4O3

Molecular Weight: 418.59

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCN(CC)NC(=O)/C=C/c1ccc(CNCCc2c(C)[nH]c3ccccc23)cc1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C26H34N4O.C2HF3O2/c1-4-18-30(5-2)29-26(31)15-14-21-10-12-22(13-11-21)19-27-17-16-23-20(3)28-25-9-7-6-8-24(23)25;3-2(4,5)1(6)7/h6-15,27-28H,4-5,16-19H2,1-3H3,(H,29,31);(H,6,7)/b15-14+;

Standard InChI Key:  AYRRLROSQLYUTL-WPDLWGESSA-N

Molfile:  

     RDKit          2D

 38 39  0  0  0  0  0  0  0  0999 V2000
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   12.8748  -19.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5866  -19.4764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8748  -18.2465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4511  -19.0678    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.1629  -20.2977    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.4489  -19.8850    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5078  -17.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2182  -16.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7956  -17.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0882  -17.2819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3761  -17.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0609  -18.6785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6487  -17.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1997  -17.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9492  -16.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481  -16.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981  -17.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8515  -17.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6375  -16.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3463  -16.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0529  -16.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7617  -16.4477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0506  -15.2240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4683  -16.0372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4660  -15.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1771  -16.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1725  -14.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8837  -16.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5926  -16.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 23  1  0
 22 19  1  0
 19 20  1  0
 20 18  2  0
 20 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 12 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 31 33  1  0
 33 34  1  0
 33 35  1  0
 34 36  1  0
 35 37  1  0
 37 38  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 418.59

Molecular Weight (Monoisotopic): 418.2733

AlogP: 4.58

#Rotatable Bonds: 11

Polar Surface Area: 60.16

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.76

CX Basic pKa: 9.71

CX LogP: 4.30

CX LogD: 2.04

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.24

Np Likeness Score: -0.68

References

1. Li X, Jiang Y, Peterson YK, Xu T, Himes RA, Luo X, Yin G, Inks ES, Dolloff N, Halene S, Chan SSL, Chou CJ..  (2020)  Design of Hydrazide-Bearing HDACIs Based on Panobinostat and Their p53 and FLT3-ITD Dependency in Antileukemia Activity.,  63  (10): [PMID:32321249] [10.1021/acs.jmedchem.0c00442]

Source

Source(1):

• Scientific Literature