2-Hydroxymethyl-5-[6-(2-pyridin-2-yl-ethylamino)-purin-9-yl]-tetrahydro-furan-3,4-diol

ID: ALA607684

PubChem CID: 46877186

Max Phase: Preclinical

Molecular Formula: C17H20N6O4

Molecular Weight: 372.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1OC(n2cnc3c(NCCc4ccccn4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C17H20N6O4/c24-7-11-13(25)14(26)17(27-11)23-9-22-12-15(20-8-21-16(12)23)19-6-4-10-3-1-2-5-18-10/h1-3,5,8-9,11,13-14,17,24-26H,4,6-7H2,(H,19,20,21)/t11-,13-,14-,17?/m1/s1

Standard InChI Key:  PUDADMJNHVWEPI-IKYDMHQPSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    5.5167   -5.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -6.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -5.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125   -4.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167   -7.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167   -6.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -7.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -6.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -4.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -5.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -4.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -5.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -2.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -8.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125   -3.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -8.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8917   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -6.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -7.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -2.7417    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  1  0
  5  7  2  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  6  1  0
 10  8  1  0
 11  4  2  0
 12  3  2  0
 13 14  2  0
 14 12  1  0
 15 19  2  0
  6 16  1  6
 17 11  1  0
  9 18  1  6
 19 20  1  0
 20 21  1  0
 21 17  1  0
 10 22  1  1
 23 22  1  0
 24 15  1  0
 25 19  1  0
 26 27  1  0
 27 25  2  0
  4  5  1  0
  9 10  1  0
 13 11  1  0
 26 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA607684

   (2R,3S,4R)-2-(hydroxymethyl)-5-[6-(2-pyridin-2-ylethylamino)purin-9-yl]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: 372.39

Molecular Weight (Monoisotopic): 372.1546

AlogP: -0.51

#Rotatable Bonds: 6

Polar Surface Area: 138.44

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 5.41

CX LogP: -0.96

CX LogD: -0.97

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: 0.07

References

1. Kusachi S, Thompson RD, Yamada N, Daly DT, Olsson RA..  (1986)  Dog coronary artery adenosine receptor: structure of the N6-aryl subregion.,  29  (6): [PMID:3012086] [10.1021/jm00156a016]

Source

Source(1):

• Scientific Literature