2-(2-Methyl-1H-indol-3-yl)-N-(4-(2-propylhydrazinecarbonyl)-benzyl)ethanaminium 2,2,2-Trifluoroacetate

ID: ALA4531072

PubChem CID: 155546022

Max Phase: Preclinical

Molecular Formula: C24H29F3N4O3

Molecular Weight: 364.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCNNC(=O)c1ccc(CNCCc2c(C)[nH]c3ccccc23)cc1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C22H28N4O.C2HF3O2/c1-3-13-24-26-22(27)18-10-8-17(9-11-18)15-23-14-12-19-16(2)25-21-7-5-4-6-20(19)21;3-2(4,5)1(6)7/h4-11,23-25H,3,12-15H2,1-2H3,(H,26,27);(H,6,7)

Standard InChI Key:  GYBOIXLUOLUHBI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   27.8836  -16.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5954  -15.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3072  -16.3603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5954  -15.1304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1717  -15.9517    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.8836  -17.1817    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.1695  -16.7689    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.5641  -13.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2733  -13.7347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5610  -12.5033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9836  -13.3193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6970  -13.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4072  -13.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1206  -13.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4318  -13.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4306  -14.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1428  -14.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8566  -14.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8538  -13.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1410  -13.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7185  -14.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0111  -14.5662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2989  -14.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5874  -14.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8753  -14.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9838  -15.9627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7873  -15.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3978  -16.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5716  -15.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1225  -14.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8720  -13.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0710  -13.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5209  -14.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7743  -15.0828    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  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 19  8  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 30  1  0
 29 26  1  0
 26 27  1  0
 27 25  2  0
 27 28  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  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: 364.49

Molecular Weight (Monoisotopic): 364.2263

AlogP: 3.45

#Rotatable Bonds: 9

Polar Surface Area: 68.95

Molecular Species: BASE

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.52

CX LogP: 3.50

CX LogD: 1.41

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.35

Np Likeness Score: -1.04

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