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

ID: ALA4474900

PubChem CID: 155537455

Max Phase: Preclinical

Molecular Formula: C26H28F3N5O3

Molecular Weight: 401.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2ccccc2c1CCNCc1ccc(/C=C/C(=O)NNCCC#N)cc1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C24H27N5O.C2HF3O2/c1-18-21(22-5-2-3-6-23(22)28-18)13-16-26-17-20-9-7-19(8-10-20)11-12-24(30)29-27-15-4-14-25;3-2(4,5)1(6)7/h2-3,5-12,26-28H,4,13,15-17H2,1H3,(H,29,30);(H,6,7)/b12-11+;

Standard InChI Key:  OJAQYXCOIGRQFF-CALJPSDSSA-N

Molfile:  

     RDKit          2D

 37 38  0  0  0  0  0  0  0  0999 V2000
   26.6495  -30.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3614  -29.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0732  -30.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3614  -28.8700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9377  -29.6913    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.6495  -30.9212    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.9355  -30.5085    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.2460  -26.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2449  -27.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9571  -28.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6709  -27.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6680  -26.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9553  -26.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5327  -28.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8254  -27.6165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1132  -28.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4017  -27.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6895  -28.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7981  -29.0130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6016  -28.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2121  -29.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3859  -28.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9368  -27.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6863  -26.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8853  -26.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3352  -27.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5886  -28.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3746  -26.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0834  -26.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7900  -26.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4989  -26.7823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7877  -25.5585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2054  -26.3717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9143  -26.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6208  -26.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3297  -26.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0418  -27.1841    0.0000 N   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
 34 35  1  0
 35 36  1  0
 36 37  3  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: 401.51

Molecular Weight (Monoisotopic): 401.2216

AlogP: 3.36

#Rotatable Bonds: 10

Polar Surface Area: 92.74

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.35

CX Basic pKa: 9.70

CX LogP: 2.90

CX LogD: 0.64

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.24

Np Likeness Score: -0.85

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