4-[2-(3,4-Dichloro-benzylamino)-6-oxo-1,6-dihydro-purin-9-yl]-butyric acid

ID: ALA182450

PubChem CID: 136048761

Max Phase: Preclinical

Molecular Formula: C16H15Cl2N5O3

Molecular Weight: 396.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCCn1cnc2c(O)nc(NCc3ccc(Cl)c(Cl)c3)nc21

Standard InChI:  InChI=1S/C16H15Cl2N5O3/c17-10-4-3-9(6-11(10)18)7-19-16-21-14-13(15(26)22-16)20-8-23(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:  MNHBIUCZFHMPGK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -1.6625    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3750   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583   -0.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625   -1.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9833    0.5208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3750   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458    1.1958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    1.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375   -1.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0958   -1.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750    2.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6000   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1250    1.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250    0.1625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000    1.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -1.2542    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4167    2.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6000   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0625    2.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  7  2  0
  5  2  1  0
  6  2  2  0
  7  3  1  0
  8  1  1  0
  9  8  1  0
 10 15  2  0
 11  7  1  0
 12  6  1  0
 13 26  1  0
 14 17  2  0
 15 18  1  0
 16 13  2  0
 17 24  1  0
 18 21  1  0
 19 10  1  0
 20  8  1  0
 21 11  1  0
 22 14  1  0
 23 13  1  0
 24 18  2  0
 25 20  1  0
 26 25  1  0
  9  5  2  0
  4  6  1  0
 14 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA182450

   ---

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: 3.67

CX Basic pKa: 1.19

CX LogP: 3.31

CX LogD: -0.01

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