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

ID: ALA181398

PubChem CID: 136048760

Max Phase: Preclinical

Molecular Formula: C21H25Cl2N5O3

Molecular Weight: 466.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H25Cl2N5O3/c1-13(2)20(30)31-9-5-3-4-8-28-12-25-18-17(28)19(29)27-21(26-18)24-11-14-6-7-15(22)16(23)10-14/h6-7,10,12-13H,3-5,8-9,11H2,1-2H3,(H2,24,26,27,29)

Standard InChI Key:  OTPAIJFBKDHHDU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    0.7375    0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -0.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7375   -1.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667    1.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458    0.4958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208    1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3083    1.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -1.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500   -1.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1250   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8583    2.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5500    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1250    0.1500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -1.2417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5208    1.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3375    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0208    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9875    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708    0.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1958    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    0.7458    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 23  1  0
 11 15  2  0
 12  7  1  0
 13  4  1  0
 14 17  2  0
 15 19  1  0
 16 10  2  0
 17 24  1  0
 18 10  1  0
 19 21  1  0
 20 11  1  0
 21 12  1  0
 22 14  1  0
 23 28  1  0
 24 19  2  0
 25  8  1  0
 26 18  1  0
 27 18  1  0
 28 30  1  0
 29 25  1  0
 30 31  1  0
 31 29  1  0
  9  8  1  0
  5  4  1  0
 14 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA181398

   ---

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: 466.37

Molecular Weight (Monoisotopic): 465.1334

AlogP: 4.82

#Rotatable Bonds: 10

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: 5.28

CX LogD: 5.28

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.33

Np Likeness Score: -1.05

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