2-(3,4-Dichloro-benzylamino)-7-(2-ethoxy-ethyl)-1,7-dihydro-purin-6-one

ID: ALA361426

PubChem CID: 136048755

Max Phase: Preclinical

Molecular Formula: C16H17Cl2N5O2

Molecular Weight: 382.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOCCn1cnc2nc(NCc3ccc(Cl)c(Cl)c3)nc(O)c21

Standard InChI:  InChI=1S/C16H17Cl2N5O2/c1-2-25-6-5-23-9-20-14-13(23)15(24)22-16(21-14)19-8-10-3-4-11(17)12(18)7-10/h3-4,7,9H,2,5-6,8H2,1H3,(H2,19,21,22,24)

Standard InChI Key:  HGCZKHBKYSHNCZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -0.5833    0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833    0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375    0.2583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833   -0.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    1.4833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083    0.8000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    1.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542   -0.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -0.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875   -0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167    0.4583    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5667   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -0.9792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7000    0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0625    1.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208    1.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4250    1.5000    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 14  2  0
 11  7  1  0
 12  4  1  0
 13 15  2  0
 14 16  1  0
 15 20  1  0
 16 18  1  0
 17 10  1  0
 18 11  1  0
 19 13  1  0
 20 16  2  0
 21  8  1  0
 22 23  1  0
 23 21  1  0
 24 22  1  0
 25 24  1  0
  9  8  1  0
  5  4  1  0
 13 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA361426

   ---

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: 382.25

Molecular Weight (Monoisotopic): 381.0759

AlogP: 3.49

#Rotatable Bonds: 7

Polar Surface Area: 85.09

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.30

CX Basic pKa: 1.98

CX LogP: 3.57

CX LogD: 3.57

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -1.66

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