2-(3,4-Dichloro-benzylamino)-7-(5-hydroxy-pentyl)-1,7-dihydro-purin-6-one

ID: ALA183459

PubChem CID: 135546623

Max Phase: Preclinical

Molecular Formula: C17H19Cl2N5O2

Molecular Weight: 396.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCCCCCn1cnc2nc(NCc3ccc(Cl)c(Cl)c3)nc(O)c21

Standard InChI:  InChI=1S/C17H19Cl2N5O2/c18-12-5-4-11(8-13(12)19)9-20-17-22-15-14(16(26)23-17)24(10-21-15)6-2-1-3-7-25/h4-5,8,10,25H,1-3,6-7,9H2,(H2,20,22,23,26)

Standard InChI Key:  ACKDITWJZRHUBF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -0.3500    0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583    0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3625    0.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583   -0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3500   -1.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250    1.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3625   -0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375    1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375   -0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -1.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -1.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.3750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7917   -0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -1.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7500    2.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2083    1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0250    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3958    1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375    0.9875    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 25  1  0
 24 21  1  0
 25 26  1  0
 26 24  1  0
  9  8  1  0
  5  4  1  0
 13 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA183459

   ---

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: 396.28

Molecular Weight (Monoisotopic): 395.0916

AlogP: 3.61

#Rotatable Bonds: 8

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: 12.33

CX Basic pKa: 2.00

CX LogP: 3.59

CX LogD: 3.59

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.50

Np Likeness Score: -1.22

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. Xu WC, Wright GE, Brown NC, Long ZY, Zhi CX, Dvoskin S, Gambino JJ, Barnes MH, Butler MM..  (2011)  7-Alkyl-N(2)-substituted-3-deazaguanines. Synthesis, DNA polymerase III inhibition and antibacterial activity.,  21  (14): [PMID:21684746] [10.1016/j.bmcl.2011.05.093]

Source

Source(1):

• Scientific Literature