2-(3,4-Dichloro-benzylamino)-9-(4-hydroxy-butyl)-1,9-dihydro-purin-6-one

ID: ALA182072

PubChem CID: 135970754

Max Phase: Preclinical

Molecular Formula: C16H17Cl2N5O2

Molecular Weight: 382.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCCCCn1cnc2c(O)nc(NCc3ccc(Cl)c(Cl)c3)nc21

Standard InChI:  InChI=1S/C16H17Cl2N5O2/c17-11-4-3-10(7-12(11)18)8-19-16-21-14-13(15(25)22-16)20-9-23(14)5-1-2-6-24/h3-4,7,9,24H,1-2,5-6,8H2,(H2,19,21,22,25)

Standard InChI Key:  MXZSROXOTCJLTP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -1.6208    0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3250    0.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125    0.0208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6208   -1.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9458    0.5708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3250   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000    1.2458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125    1.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958   -1.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0458   -1.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792    0.2208    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -1.2167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458    1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625    2.7583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167    2.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375    1.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042    2.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  7  2  0
  5  2  1  0
  6  2  2  0
  7  3  1  0
  8  1  1  0
  9  8  1  0
 10 14  2  0
 11  7  1  0
 12  6  1  0
 13 15  2  0
 14 16  1  0
 15 21  1  0
 16 18  1  0
 17 10  1  0
 18 11  1  0
 19 13  1  0
 20  8  1  0
 21 16  2  0
 22 23  1  0
 23 25  1  0
 24 20  1  0
 25 24  1  0
  9  5  2  0
  4  6  1  0
 13 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA182072

   ---

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: 3.22

#Rotatable Bonds: 7

Polar Surface Area: 96.09

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.56

CX Basic pKa: 0.88

CX LogP: 3.19

CX LogD: 3.19

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.54

Np Likeness Score: -1.31

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]

2. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Pandemic Response Box,  [10.6019/CHEMBL4513161]

Source

Source(2):

• Scientific Literature
• CO-ADD antimicrobial screening data