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

ID: ALA369308

PubChem CID: 136048759

Max Phase: Preclinical

Molecular Formula: C20H23Cl2N5O3

Molecular Weight: 452.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H](C)CCCCn1cnc2nc(NCc3ccc(Cl)c(Cl)c3)nc(O)c21

Standard InChI:  InChI=1S/C20H23Cl2N5O3/c1-12(30-13(2)28)5-3-4-8-27-11-24-18-17(27)19(29)26-20(25-18)23-10-14-6-7-15(21)16(22)9-14/h6-7,9,11-12H,3-5,8,10H2,1-2H3,(H2,23,25,26,29)/t12-/m1/s1

Standard InChI Key:  DTVTYYCEPYWSHN-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  1  0  0  0  0  0999 V2000
    0.3792    0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -0.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -1.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2000    1.0708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9500    0.3958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125    1.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -1.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500   -1.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7833    2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9750    2.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0208    1.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792    0.0458    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -1.3917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7500    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4750    1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3458    3.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3000    0.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6625    1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7208    0.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1125    0.6625    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 17  1  0
 14 18  2  0
 15 19  1  0
 16 13  2  0
 17 25  1  0
 18 23  1  0
 19 21  1  0
 20 10  1  0
 21 11  1  0
 22 14  1  0
 23 19  2  0
 24  8  1  0
 25 28  1  0
 26 13  1  0
 27 24  1  0
 28 30  1  0
 25 29  1  1
 30 27  1  0
  9  8  1  0
  5  4  1  0
 14 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA369308

   ---

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: 452.34

Molecular Weight (Monoisotopic): 451.1178

AlogP: 4.57

#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: 4.45

CX LogD: 4.45

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: -0.83

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