4-[2-(3,4-Dichloro-benzylamino)-6-oxo-1,6-dihydro-purin-7-yl]-butyric acid

ID: ALA182499

PubChem CID: 136048757

Max Phase: Preclinical

Molecular Formula: C16H15Cl2N5O3

Molecular Weight: 396.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCCn1cnc2nc(NCc3ccc(Cl)c(Cl)c3)nc(O)c21

Standard InChI:  InChI=1S/C16H15Cl2N5O3/c17-10-4-3-9(6-11(10)18)7-19-16-21-14-13(15(26)22-16)23(8-20-14)5-1-2-12(24)25/h3-4,6,8H,1-2,5,7H2,(H,24,25)(H2,19,21,22,26)

Standard InChI Key:  ZJLYMFQTKOGRKN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -0.4083    0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042    0.1625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -1.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    1.3833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333    0.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083    1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167   -1.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -1.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4583    1.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083    2.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    0.3583    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7292   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -1.0792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333    0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2708    1.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0958    1.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9000    0.9625    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 26  1  0
 14 17  2  0
 15 18  1  0
 16 13  2  0
 17 24  1  0
 18 20  1  0
 19 10  1  0
 20 11  1  0
 21 14  1  0
 22  8  1  0
 23 13  1  0
 24 18  2  0
 25 22  1  0
 26 25  1  0
  9  8  1  0
  5  4  1  0
 14 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA182499

   ---

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: 396.23

Molecular Weight (Monoisotopic): 395.0552

AlogP: 3.32

#Rotatable Bonds: 7

Polar Surface Area: 113.16

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.68

CX Basic pKa: 2.07

CX LogP: 3.12

CX LogD: -0.06

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.56

Np Likeness Score: -1.32

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