3-(4-Hydroxybutyl)-6-(4-(trifluoromethyl)phenyl)-3,5-dihydro-9H-imidazo[1,2-a]purin-9-one

ID: ALA4591403

PubChem CID: 155568742

Max Phase: Preclinical

Molecular Formula: C18H16F3N5O2

Molecular Weight: 391.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1c2ncn(CCCCO)c2nc2[nH]c(-c3ccc(C(F)(F)F)cc3)cn12

Standard InChI:  InChI=1S/C18H16F3N5O2/c19-18(20,21)12-5-3-11(4-6-12)13-9-26-16(28)14-15(24-17(26)23-13)25(10-22-14)7-1-2-8-27/h3-6,9-10,27H,1-2,7-8H2,(H,23,24)

Standard InChI Key:  QOBIDFBVJKCQST-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   43.5934  -27.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5851  -26.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8752  -28.1076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.3693  -26.6136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.3775  -27.9467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.8752  -26.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8563  -27.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3693  -28.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8752  -25.6437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.0750  -29.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7890  -28.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.2088  -28.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.4989  -29.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1653  -27.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1608  -26.8737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.3823  -26.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9056  -27.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3896  -27.9475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6815  -27.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0884  -27.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6810  -26.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8625  -26.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8661  -27.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4588  -27.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6417  -27.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2299  -26.5910    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.2363  -28.0064    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.8231  -27.2934    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  1  1  0
  6  2  1  0
 14  3  2  0
  7  5  1  0
  8  5  1  0
  9  6  2  0
 10  8  1  0
 11 10  1  0
 12 13  1  0
 13 11  1  0
  7  4  2  0
 15  6  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  1  0
 23 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 24  2  0
 20 17  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4591403

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 391.35

Molecular Weight (Monoisotopic): 391.1256

AlogP: 2.83

#Rotatable Bonds: 5

Polar Surface Area: 88.21

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.10

CX Basic pKa: 1.42

CX LogP: 1.83

CX LogD: 1.83

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.51

Np Likeness Score: -0.93

References

1. Mohammed AF, Andrei G, Hayallah AM, Abdel-Moty SG, Snoeck R, Simons C..  (2019)  Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.,  27  (6): [PMID:30738653] [10.1016/j.bmc.2019.02.005]

Source

Source(1):

• Scientific Literature