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

ID: ALA182401

PubChem CID: 135522323

Max Phase: Preclinical

Molecular Formula: C16H17Cl2N5O2

Molecular Weight: 382.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCCCCn1cnc2nc(NCc3ccc(Cl)c(Cl)c3)nc(O)c21

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

Standard InChI Key:  SIJYBMLNZYHCPV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -0.5833    0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833    0.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292    0.2583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833   -0.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583    1.4833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958    0.8083    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
    3.5042   -0.2667    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
   -2.0083   -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
    2.6792   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -1.6917    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    0.4458    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5667   -0.5667    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   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4333    1.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208    1.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2583    1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0708    1.0708    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 24  1  0
  9  8  1  0
  5  4  1  0
 13 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA182401

   ---

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: 12.33

CX Basic pKa: 2.00

CX LogP: 3.15

CX LogD: 3.15

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. 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