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

ID: ALA16026

PubChem CID: 135435086

Max Phase: Preclinical

Molecular Formula: C14H15N5O

Molecular Weight: 269.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(O)c3[nH]cnc3n2)ccc1C

Standard InChI:  InChI=1S/C14H15N5O/c1-3-9-6-10(5-4-8(9)2)17-14-18-12-11(13(20)19-14)15-7-16-12/h4-7H,3H2,1-2H3,(H3,15,16,17,18,19,20)

Standard InChI Key:  JUIJZZPKQVQVDL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    2.7875   -3.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2750   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2750   -2.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375   -2.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -3.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -2.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -1.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500   -3.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -5.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -5.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375   -5.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -5.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  4  2  0
  6  5  1  0
  7  3  1  0
  8  2  1  0
  9  8  2  0
 10  4  1  0
 11 14  2  0
 12  6  1  0
 13 10  1  0
 14 13  1  0
 15 16  2  0
 16 17  1  0
 17 13  2  0
 18 11  1  0
 19 15  1  0
 20 18  1  0
  6  3  2  0
  7  9  1  0
 15 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA16026

   ---

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: 269.31

Molecular Weight (Monoisotopic): 269.1277

AlogP: 2.67

#Rotatable Bonds: 3

Polar Surface Area: 86.72

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.95

CX Basic pKa: 1.71

CX LogP: 3.54

CX LogD: 3.54

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.68

Np Likeness Score: -1.14

References

1. Wright GE, Dudycz LW, Kazimierczuk Z, Brown NC, Khan NN..  (1987)  Synthesis, cell growth inhibition, and antitumor screening of 2-(p-n-butylanilino)purines and their nucleoside analogues.,  30  (1): [PMID:3806587] [10.1021/jm00384a019]

2. Focher F, Hildebrand C, Freese S, Ciarrocchi G, Noonan T, Sangalli S, Brown N, Spadari S, Wright G..  (1988)  N2-phenyldeoxyguanosine: a novel selective inhibitor of herpes simplex thymidine kinase.,  31  (8): [PMID:2840499] [10.1021/jm00403a004]

3. Hildebrand C, Sandoli D, Focher F, Gambino J, Ciarrocchi G, Spadari S, Wright G..  (1990)  Structure-activity relationships of N2-substituted guanines as inhibitors of HSV1 and HSV2 thymidine kinases.,  33  (1): [PMID:2153203] [10.1021/jm00163a033]

4. Gambino J, Focher F, Hildebrand C, Maga G, Noonan T, Spadari S, Wright G..  (1992)  Quantitative structure-activity relationships of N2-phenylguanines as inhibitors of herpes simplex virus thymidine kinases.,  35  (16): [PMID:1323680] [10.1021/jm00094a007]

5. 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