2-(6-Amino-8-ethyl-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA608037

PubChem CID: 46875851

Max Phase: Preclinical

Molecular Formula: C12H17N5O4

Molecular Weight: 295.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nc2c(N)ncnc2n1C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C12H17N5O4/c1-2-6-16-7-10(13)14-4-15-11(7)17(6)12-9(20)8(19)5(3-18)21-12/h4-5,8-9,12,18-20H,2-3H2,1H3,(H2,13,14,15)/t5-,8-,9-,12?/m1/s1

Standard InChI Key:  OOOZBXHUEHEQJT-BIOSCVOMSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    2.6125   -2.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -4.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125   -1.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -4.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -2.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000   -2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -5.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167   -5.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2125   -3.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  2  0
  5  6  2  0
  6  1  1  0
  7  2  1  0
  8  2  1  0
  9  7  1  0
 10  8  1  0
 11  3  1  0
 12  4  1  0
 13 14  1  0
 14 11  2  0
  7 15  1  6
 16 12  1  0
  9 17  1  6
 18  6  1  0
 10 19  1  1
 20 19  1  0
 21 18  1  0
  4  5  1  0
  9 10  1  0
 12 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA608037

   (3R,4S,5R)-2-(6-amino-8-ethylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

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: 295.30

Molecular Weight (Monoisotopic): 295.1281

AlogP: -1.42

#Rotatable Bonds: 3

Polar Surface Area: 139.54

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 3.84

CX LogP: -1.27

CX LogD: -1.27

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.54

Np Likeness Score: 0.56

References

1. Van Aerschot AA, Mamos P, Weyns NJ, Ikeda S, De Clercq E, Herdewijn PA..  (1993)  Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents.,  36  (20): [PMID:8411010] [10.1021/jm00072a013]

Source

Source(1):

• Scientific Literature