5-((2-(1H-indol-3-yl)ethylamino)methylene)-1-(4-bromophenyl)pyrimidine-2,4,6(1H,3H,5H)-trione

ID: ALA4525557

PubChem CID: 5194305

Max Phase: Preclinical

Molecular Formula: C21H17BrN4O3

Molecular Weight: 453.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)N(c2ccc(Br)cc2)C(=O)/C1=C\NCCc1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C21H17BrN4O3/c22-14-5-7-15(8-6-14)26-20(28)17(19(27)25-21(26)29)12-23-10-9-13-11-24-18-4-2-1-3-16(13)18/h1-8,11-12,23-24H,9-10H2,(H,25,27,29)/b17-12-

Standard InChI Key:  ZRLVXELLJVASOQ-ATVHPVEESA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   20.9773  -22.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9761  -23.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6842  -23.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3938  -23.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3910  -22.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6824  -21.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6845  -24.4309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9749  -24.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9728  -25.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6786  -26.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3882  -25.6572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3920  -24.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2634  -26.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5574  -25.6461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8480  -26.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1420  -25.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4326  -26.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5458  -27.0300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3458  -26.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1401  -26.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6899  -25.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4416  -24.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6439  -24.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0949  -25.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3461  -26.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6753  -26.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1002  -24.4297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2683  -24.4277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6800  -21.1641    0.0000 Br  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
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  3  7  1  0
  9 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 21  1  0
 20 18  1  0
 18 19  1  0
 19 17  2  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 10 26  2  0
 12 27  2  0
  8 28  2  0
  6 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4525557

   1-(4-bromophenyl)-5-({[2-(1H-indol-3-yl)ethyl]amino}methylene)-2,4,6(1H,3H,5H)-pyrimidinetrione

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: 453.30

Molecular Weight (Monoisotopic): 452.0484

AlogP: 3.23

#Rotatable Bonds: 5

Polar Surface Area: 94.30

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.69

CX Basic pKa: ┄

CX LogP: 3.15

CX LogD: 2.38

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.31

Np Likeness Score: -1.11

References

1. Wang Y, Dou X, Jiang L, Jin H, Zhang L, Zhang L, Liu Z..  (2019)  Discovery of novel glycogen synthase kinase-3α inhibitors: Structure-based virtual screening, preliminary SAR and biological evaluation for treatment of acute myeloid leukemia.,  171  [PMID:30925338] [10.1016/j.ejmech.2019.03.039]

Source

Source(1):

• Scientific Literature