4-[2-(3,4-Dichloro-benzylamino)-6-oxo-1,6-dihydro-purin-7-yl]-butyric acid ethyl ester

ID: ALA181045

PubChem CID: 136048752

Max Phase: Preclinical

Molecular Formula: C18H19Cl2N5O3

Molecular Weight: 424.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CCCn1cnc2nc(NCc3ccc(Cl)c(Cl)c3)nc(O)c21

Standard InChI:  InChI=1S/C18H19Cl2N5O3/c1-2-28-14(26)4-3-7-25-10-22-16-15(25)17(27)24-18(23-16)21-9-11-5-6-12(19)13(20)8-11/h5-6,8,10H,2-4,7,9H2,1H3,(H2,21,23,24,27)

Standard InChI Key:  RADAFPBWNKQHEY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    0.0375    0.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    0.0208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375   -1.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458    1.2458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875    0.5708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9625    1.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -1.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -1.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0208    1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7583    2.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5250    0.2208    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1750   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -1.2167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875    0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8125    1.2708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6500    1.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4500    0.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3708    1.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1667    1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  2  0
  5  7  2  0
  6  1  1  0
  7  3  1  0
  8  2  1  0
  9  6  2  0
 10 15  2  0
 11  7  1  0
 12  4  1  0
 13 26  1  0
 14 17  2  0
 15 18  1  0
 16 13  2  0
 17 23  1  0
 18 20  1  0
 19 10  1  0
 20 11  1  0
 21 14  1  0
 22  8  1  0
 23 18  2  0
 24 13  1  0
 25 22  1  0
 26 25  1  0
 27 24  1  0
 28 27  1  0
  9  8  1  0
  5  4  1  0
 14 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA181045

   ---

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: 424.29

Molecular Weight (Monoisotopic): 423.0865

AlogP: 3.79

#Rotatable Bonds: 8

Polar Surface Area: 102.16

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.49

CX Basic pKa: 2.09

CX LogP: 3.77

CX LogD: 3.77

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: -1.36

References

1. Wright GE, Brown NC, Xu WC, Long ZY, Zhi C, Gambino JJ, Barnes MH, Butler MM..  (2005)  Active site directed inhibitors of replication-specific bacterial DNA polymerases.,  15  (3): [PMID:15664846] [10.1016/j.bmcl.2004.11.016]

Source

Source(1):

• Scientific Literature