(R,E)-N-(4-(3-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)piperidin-1-yl)phenyl)-4-(dimethylamino)but-2-enamide

ID: ALA4866812

PubChem CID: 134543415

Max Phase: Preclinical

Molecular Formula: C29H32ClN7O

Molecular Weight: 530.08

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)C/C=C/C(=O)Nc1ccc(N2CCC[C@@H](Nc3ncc(Cl)c(-c4c[nH]c5ccccc45)n3)C2)cc1

Standard InChI:  InChI=1S/C29H32ClN7O/c1-36(2)15-6-10-27(38)33-20-11-13-22(14-12-20)37-16-5-7-21(19-37)34-29-32-18-25(30)28(35-29)24-17-31-26-9-4-3-8-23(24)26/h3-4,6,8-14,17-18,21,31H,5,7,15-16,19H2,1-2H3,(H,33,38)(H,32,34,35)/b10-6+/t21-/m1/s1

Standard InChI Key:  VFUSOVNUCLAYBM-VMLCMGRWSA-N

Molfile:  

 
     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
   35.0732  -14.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0721  -15.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7874  -15.4802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5043  -15.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5015  -14.2355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7855  -13.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2199  -15.4783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.9343  -15.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6443  -15.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3564  -15.0690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3595  -14.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6440  -13.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9256  -14.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0705  -15.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3596  -15.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4649  -16.4747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2726  -16.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0527  -15.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6037  -15.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3512  -14.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5480  -14.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9979  -14.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2532  -15.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3581  -13.8265    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   40.0652  -16.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7785  -16.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4954  -16.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4946  -15.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7807  -15.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2099  -16.7249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.9253  -16.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6399  -16.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9260  -15.4871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.3552  -16.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0698  -16.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7852  -16.3152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   46.4998  -16.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7859  -15.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  8  7  1  6
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 10 14  1  0
 15 19  1  0
 18 16  1  0
 16 17  1  0
 17 15  2  0
  2 15  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  1 24  1  0
 14 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 14  1  0
 27 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 32 34  2  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4866812

   ---

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: 530.08

Molecular Weight (Monoisotopic): 529.2357

AlogP: 5.42

#Rotatable Bonds: 8

Polar Surface Area: 89.18

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.81

CX LogP: 5.12

CX LogD: 3.70

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.26

Np Likeness Score: -1.21

References

1. Jiang B, Jiang J, Kaltheuner IH, Iniguez AB, Anand K, Ferguson FM, Ficarro SB, Seong BKA, Greifenberg AK, Dust S, Kwiatkowski NP, Marto JA, Stegmaier K, Zhang T, Geyer M, Gray NS..  (2021)  Structure-activity relationship study of THZ531 derivatives enables the discovery of BSJ-01-175 as a dual CDK12/13 covalent inhibitor with efficacy in Ewing sarcoma.,  221  [PMID:33945934] [10.1016/j.ejmech.2021.113481]

Source

Source(1):

• Scientific Literature