Acetic acid 5-[2-(3,4-dichloro-benzylamino)-6-oxo-1,6-dihydro-purin-7-yl]-pentyl ester

ID: ALA361838

PubChem CID: 135524957

Max Phase: Preclinical

Molecular Formula: C19H21Cl2N5O3

Molecular Weight: 438.32

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H21Cl2N5O3/c1-12(27)29-8-4-2-3-7-26-11-23-17-16(26)18(28)25-19(24-17)22-10-13-5-6-14(20)15(21)9-13/h5-6,9,11H,2-4,7-8,10H2,1H3,(H2,22,24,25,28)

Standard InChI Key:  DRTFCWGXCOANMR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    0.3542    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3458   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667   -0.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3458   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542   -1.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792    1.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9625    0.5458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917   -1.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708   -1.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8458    1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4000    2.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542    0.1833    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -1.2417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0458    1.8458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708    0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0917    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4958    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6833    1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333    0.8000    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 23  1  0
 14 17  2  0
 15 18  1  0
 16 13  2  0
 17 22  1  0
 18 20  1  0
 19 10  1  0
 20 11  1  0
 21 14  1  0
 22 18  2  0
 23 26  1  0
 24  8  1  0
 25 13  1  0
 26 28  1  0
 27 24  1  0
 28 29  1  0
 29 27  1  0
  9  8  1  0
  5  4  1  0
 14 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA361838

   ---

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: 438.32

Molecular Weight (Monoisotopic): 437.1021

AlogP: 4.18

#Rotatable Bonds: 9

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: 12.33

CX Basic pKa: 2.00

CX LogP: 4.03

CX LogD: 4.03

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -1.06

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