2-(3-Ethyl-4-methyl-phenylamino)-9-(4-hydroxy-butyl)-1,9-dihydro-purin-6-one

ID: ALA180736

PubChem CID: 136132271

Max Phase: Preclinical

Molecular Formula: C18H23N5O2

Molecular Weight: 341.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(O)c3ncn(CCCCO)c3n2)ccc1C

Standard InChI:  InChI=1S/C18H23N5O2/c1-3-13-10-14(7-6-12(13)2)20-18-21-16-15(17(25)22-18)19-11-23(16)8-4-5-9-24/h6-7,10-11,24H,3-5,8-9H2,1-2H3,(H2,20,21,22,25)

Standard InChI Key:  KRGAMUUUYRRPMP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -1.5333    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208   -0.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -1.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8583    0.5333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083    1.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208    1.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -1.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583   -1.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542    2.7208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542    0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042    2.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3458    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917    2.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792    0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  3  1  0
  5  4  2  0
  6  2  1  0
  7  2  2  0
  8  1  1  0
  9  8  1  0
 10  4  1  0
 11 14  2  0
 12  7  1  0
 13 10  1  0
 14 13  1  0
 15 16  2  0
 16 17  1  0
 17 13  2  0
 18  8  1  0
 19 22  1  0
 20 11  1  0
 21 15  1  0
 22 24  1  0
 23 18  1  0
 24 23  1  0
 25 20  1  0
  9  6  2  0
  5  7  1  0
 15 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA180736

   ---

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: 341.42

Molecular Weight (Monoisotopic): 341.1852

AlogP: 2.92

#Rotatable Bonds: 7

Polar Surface Area: 96.09

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.49

CX Basic pKa: 0.85

CX LogP: 3.70

CX LogD: 3.70

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.57

Np Likeness Score: -1.15

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