6-(3-Ethyl-4-methyl-phenylamino)-3-(4-piperazin-1-yl-butyl)-1H-pyrimidine-2,4-dione; Dihydrochloride

ID: ALA553529

PubChem CID: 23499112

Max Phase: Preclinical

Molecular Formula: C21H33Cl2N5O2

Molecular Weight: 385.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2cc(=O)n(CCCCN3CCNCC3)c(=O)[nH]2)ccc1C.Cl.Cl

Standard InChI:  InChI=1S/C21H31N5O2.2ClH/c1-3-17-14-18(7-6-16(17)2)23-19-15-20(27)26(21(28)24-19)11-5-4-10-25-12-8-22-9-13-25;;/h6-7,14-15,22-23H,3-5,8-13H2,1-2H3,(H,24,28);2*1H

Standard InChI Key:  WHLYGGDQJREEDK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
   10.2876   -2.6376    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4972    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007    1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875   -7.5110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4920   -0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1903   -1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8939   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1895   -7.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4885   -5.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7876   -6.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4885   -8.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7980    1.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5291   -1.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8004    2.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7876   -2.6376    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  2  6  1  0
  5  7  2  0
  6  7  1  0
  5  8  1  0
  3  9  2  0
  6 12  2  0
  8 13  1  0
 11 14  2  0
 13 14  1  0
 11 16  1  0
 16 17  2  0
  2 18  1  0
 13 19  2  0
 17 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
 15 23  1  0
 22 23  1  0
 15 24  1  0
 21 24  1  0
 11 25  1  0
 16 26  1  0
 18 27  1  0
 20 28  1  0
 27 28  1  0
 25 29  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 385.51

Molecular Weight (Monoisotopic): 385.2478

AlogP: 1.84

#Rotatable Bonds: 8

Polar Surface Area: 82.16

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.62

CX Basic pKa: 9.33

CX LogP: 2.29

CX LogD: 0.53

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: -1.15

References

1. Zhi C, Long ZY, Gambino J, Xu WC, Brown NC, Barnes M, Butler M, LaMarr W, Wright GE..  (2003)  Synthesis of substituted 6-anilinouracils and their inhibition of DNA polymerase IIIC and Gram-positive bacterial growth.,  46  (13): [PMID:12801236] [10.1021/jm020591z]

Source

Source(1):

• Scientific Literature