1-[3-[4-[3-(5-cyano-2,4-dioxo-pyrimidin-1-yl)propyl]piperazin-1-yl]propyl]-2,4-dioxo-pyrimidine-5-carbonitrile

ID: ALA4553913

PubChem CID: 1815303

Max Phase: Preclinical

Molecular Formula: C20H24N8O4

Molecular Weight: 440.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1cn(CCCN2CCN(CCCn3cc(C#N)c(=O)[nH]c3=O)CC2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C20H24N8O4/c21-11-15-13-27(19(31)23-17(15)29)5-1-3-25-7-9-26(10-8-25)4-2-6-28-14-16(12-22)18(30)24-20(28)32/h13-14H,1-10H2,(H,23,29,31)(H,24,30,32)

Standard InChI Key:  KZMACHSVSZJBQQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   31.3291   -2.5135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3339   -3.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0433   -3.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7540   -3.3369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7516   -2.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4670   -3.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1776   -3.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8865   -3.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6173   -2.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9054   -2.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   35.5972   -3.3287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3059   -3.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0144   -3.3328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0163   -2.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3034   -2.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5887   -2.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7802   -2.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0705   -2.5063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0662   -3.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7779   -3.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4938   -3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3020   -1.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3024   -0.4606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7791   -4.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7763   -5.3822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3041   -4.5654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.7285   -2.1032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7843   -1.2799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3529   -3.7380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 13 20  1  0
 13 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 25 26  3  0
 18 25  1  0
 27 28  3  0
 23 27  1  0
 15 29  2  0
 17 30  2  0
 20 31  2  0
 22 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4553913

   1-[3-[4-[3-(5-Cyano-2,4-dioxopyrimidin-1-yl)propyl]piperazin-1-yl]propyl]-2,4-dioxopyrimidine-5-carbonitrile

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: 440.46

Molecular Weight (Monoisotopic): 440.1921

AlogP: -1.77

#Rotatable Bonds: 8

Polar Surface Area: 163.78

Molecular Species: ACID

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.39

CX Basic pKa: 7.95

CX LogP: -4.31

CX LogD: -5.25

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: -0.94

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