2-[6-(2,5-Dichloro-benzylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA610294

PubChem CID: 46877195

Max Phase: Preclinical

Molecular Formula: C17H17Cl2N5O4

Molecular Weight: 426.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1OC(n2cnc3c(NCc4cc(Cl)ccc4Cl)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C17H17Cl2N5O4/c18-9-1-2-10(19)8(3-9)4-20-15-12-16(22-6-21-15)24(7-23-12)17-14(27)13(26)11(5-25)28-17/h1-3,6-7,11,13-14,17,25-27H,4-5H2,(H,20,21,22)/t11-,13-,14-,17?/m1/s1

Standard InChI Key:  WFTOPZOVBLXOPJ-IKYDMHQPSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    5.2667   -5.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917   -5.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6875   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2625   -4.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -7.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -4.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -6.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -7.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -5.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -4.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1625   -3.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500   -5.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -7.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -7.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -2.6667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -6.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -1.4417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -6.8292    0.0000 O   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 16  2  0
 14 18  1  0
 15 11  1  0
 16 12  1  0
 17 14  1  0
 18 15  1  0
 19 14  2  0
  6 20  1  6
 21 17  2  0
  9 22  1  6
 23 19  1  0
 24 17  1  0
 25 23  2  0
 10 26  1  1
 27 23  1  0
 28 26  1  0
  4  5  1  0
  9 10  1  0
 13 11  1  0
 25 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA610294

   (3R,4S,5R)-2-[6-[(2,5-dichlorophenyl)methylamino]purin-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: 426.26

Molecular Weight (Monoisotopic): 425.0658

AlogP: 1.36

#Rotatable Bonds: 5

Polar Surface Area: 125.55

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 3.72

CX LogP: 1.14

CX LogD: 1.14

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.48

Np Likeness Score: -0.04

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