tert-Butyl (2-(2-Methyl-1H-indol-3-yl)ethyl)(4-(2-propylhydrazinecarbonyl)benzyl)carbamate

ID: ALA4555545

PubChem CID: 155557199

Max Phase: Preclinical

Molecular Formula: C27H36N4O3

Molecular Weight: 464.61

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCNNC(=O)c1ccc(CN(CCc2c(C)[nH]c3ccccc23)C(=O)OC(C)(C)C)cc1

Standard InChI:  InChI=1S/C27H36N4O3/c1-6-16-28-30-25(32)21-13-11-20(12-14-21)18-31(26(33)34-27(3,4)5)17-15-22-19(2)29-24-10-8-7-9-23(22)24/h7-14,28-29H,6,15-18H2,1-5H3,(H,30,32)

Standard InChI Key:  NFDKSFRHUFVEBS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   11.3800  -13.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0892  -13.8544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3769  -12.6230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7995  -13.4390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5129  -13.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2232  -13.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9365  -13.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2477  -13.8633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2466  -14.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9587  -15.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6725  -14.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6697  -13.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9569  -13.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5344  -15.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8270  -14.6859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1149  -15.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4033  -14.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6912  -15.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997  -16.0824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6032  -15.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2138  -16.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875  -15.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9384  -14.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6879  -13.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8869  -13.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368  -14.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5902  -15.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8277  -13.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5357  -13.4524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1161  -13.4513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5363  -12.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2485  -12.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8290  -12.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5310  -11.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  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
 12  1  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
 15 28  1  0
 28 29  1  0
 28 30  2  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4555545

   ---

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: 464.61

Molecular Weight (Monoisotopic): 464.2787

AlogP: 5.10

#Rotatable Bonds: 9

Polar Surface Area: 86.46

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.87

CX LogP: 4.78

CX LogD: 4.78

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.30

Np Likeness Score: -1.21

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