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

ID: ALA4443074

PubChem CID: 155516139

Max Phase: Preclinical

Molecular Formula: C24H29F3N4O3

Molecular Weight: 364.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCNNC(=O)c1cccc(CNCCc2c(C)[nH]c3ccccc23)c1.O=C(O)C(F)(F)F

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

Standard InChI Key:  ZOMRKQFCDNFUKK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   27.0416  -26.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7534  -25.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4653  -26.3111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7534  -25.0812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3298  -25.9025    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.0416  -27.1324    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.3276  -26.7197    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.7042  -22.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7030  -22.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4152  -23.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1290  -22.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1262  -22.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4134  -21.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9909  -23.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2835  -22.9733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5713  -23.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8598  -22.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1477  -23.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2562  -24.3699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0597  -24.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6702  -24.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8440  -23.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3949  -23.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1444  -22.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3434  -22.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7933  -22.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0467  -23.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8368  -23.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8371  -24.1996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5444  -22.9736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2522  -23.3819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9598  -22.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6677  -23.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3752  -22.9727    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
 11 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  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: 9.20

CX LogP: 3.50

CX LogD: 1.71

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.35

Np Likeness Score: -1.13

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