2-Hydroxymethyl-5-{6-[2-(3-trifluoromethyl-phenyl)-ethylamino]-purin-9-yl}-tetrahydro-furan-3,4-diol

ID: ALA610049

PubChem CID: 46877192

Max Phase: Preclinical

Molecular Formula: C19H20F3N5O4

Molecular Weight: 439.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1OC(n2cnc3c(NCCc4cccc(C(F)(F)F)c4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H20F3N5O4/c20-19(21,22)11-3-1-2-10(6-11)4-5-23-16-13-17(25-8-24-16)27(9-26-13)18-15(30)14(29)12(7-28)31-18/h1-3,6,8-9,12,14-15,18,28-30H,4-5,7H2,(H,23,24,25)/t12-,14-,15-,18?/m1/s1

Standard InChI Key:  CLSROXFGGUSAJT-PZGKNFOESA-N

Molfile:  

     RDKit          2D

 31 34  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
    2.3167   -2.1417    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
    2.3167   -2.7417    0.0000 C   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
    2.8500   -3.0375    0.0000 C   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
    2.3125   -1.6000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -1.7417    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -1.7542    0.0000 F   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
    4.3500   -8.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -3.6375    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
    3.8917   -3.6292    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
    1.8125   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -3.9417    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 15  1  0
 12  4  2  0
 13  3  2  0
 14 16  2  0
 15 17  1  0
 16 13  1  0
 17 24  2  0
  6 18  1  6
 19 11  1  0
 20 11  1  0
 21 11  1  0
 22 12  1  0
  9 23  1  6
 24 30  1  0
 10 25  1  1
 26 22  1  0
 27 25  1  0
 28 29  1  0
 29 31  2  0
 30 26  1  0
 31 24  1  0
  4  5  1  0
  9 10  1  0
 14 12  1  0
 15 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA610049

   (2R,3S,4R)-2-(hydroxymethyl)-5-[6-[2-[3-(trifluoromethyl)phenyl]ethylamino]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: 439.39

Molecular Weight (Monoisotopic): 439.1467

AlogP: 1.11

#Rotatable Bonds: 6

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: 3.76

CX LogP: 1.10

CX LogD: 1.10

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.45

Np Likeness Score: 0.03

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