6-(Benzo[d][1,3]dioxol-5-yl)-3-(4-hydroxybutyl)-3,5-dihydro-9H-imidazo[1,2-a]purin-9-one

ID: ALA4531506

PubChem CID: 155546542

Max Phase: Preclinical

Molecular Formula: C18H17N5O4

Molecular Weight: 367.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1c2ncn(CCCCO)c2nc2[nH]c(-c3ccc4c(c3)OCO4)cn12

Standard InChI:  InChI=1S/C18H17N5O4/c24-6-2-1-5-22-9-19-15-16(22)21-18-20-12(8-23(18)17(15)25)11-3-4-13-14(7-11)27-10-26-13/h3-4,7-9,24H,1-2,5-6,10H2,(H,20,21)

Standard InChI Key:  XDJPONKVTLGALL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   20.8193   -4.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8111   -3.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1012   -4.8590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5952   -3.3649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6035   -4.6980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1012   -3.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0822   -4.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5952   -5.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1012   -2.3950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3010   -5.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0150   -5.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4348   -5.5441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7249   -5.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3913   -4.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3868   -3.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6082   -3.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1315   -4.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6155   -4.6988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9074   -4.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3143   -4.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9070   -3.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0884   -3.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0969   -4.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6848   -4.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8903   -4.2196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8113   -5.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5570   -5.3546    0.0000 O   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
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 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
 26 27  1  0
 27 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4531506

   ---

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: 367.37

Molecular Weight (Monoisotopic): 367.1281

AlogP: 1.54

#Rotatable Bonds: 5

Polar Surface Area: 106.67

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.11

CX Basic pKa: 1.90

CX LogP: 0.57

CX LogD: 0.57

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -0.47

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