2-Hydroxymethyl-5-{6-[(pyridin-3-ylmethyl)-amino]-purin-9-yl}-tetrahydro-furan-3,4-diol

ID: ALA609945

PubChem CID: 10109035

Max Phase: Preclinical

Molecular Formula: C16H18N6O4

Molecular Weight: 358.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1OC(n2cnc3c(NCc4cccnc4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H18N6O4/c23-6-10-12(24)13(25)16(26-10)22-8-21-11-14(19-7-20-15(11)22)18-5-9-2-1-3-17-4-9/h1-4,7-8,10,12-13,16,23-25H,5-6H2,(H,18,19,20)/t10-,12-,13-,16?/m1/s1

Standard InChI Key:  OGGGQWLDZCHKIQ-AARXTDBFSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    5.2292   -5.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -4.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -4.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -7.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5875   -4.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -6.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4292   -7.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -5.2875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -4.3792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -3.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -4.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -1.6875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -7.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -7.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -6.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -2.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -1.7000    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 15  2  0
 14 11  1  0
 15 12  1  0
 16 22  1  0
  6 17  1  6
 18 20  1  0
  9 19  1  6
 20 14  1  0
 10 21  1  1
 22 18  2  0
 23 21  1  0
 24 26  1  0
 25 18  1  0
 26 25  2  0
  4  5  1  0
  9 10  1  0
 13 11  1  0
 24 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA609945

   (2R,3S,4R)-2-(hydroxymethyl)-5-[6-(pyridin-3-ylmethylamino)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: 358.36

Molecular Weight (Monoisotopic): 358.1390

AlogP: -0.56

#Rotatable Bonds: 5

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: 5.06

CX LogP: -1.28

CX LogD: -1.28

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.47

Np Likeness Score: 0.21

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