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

ID: ALA610811

PubChem CID: 46877205

Max Phase: Preclinical

Molecular Formula: C18H21N5O4

Molecular Weight: 371.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(Nc2ncnc3c2ncn3C2O[C@H](CO)[C@@H](O)[C@H]2O)c(C)c1

Standard InChI:  InChI=1S/C18H21N5O4/c1-9-3-4-11(10(2)5-9)22-16-13-17(20-7-19-16)23(8-21-13)18-15(26)14(25)12(6-24)27-18/h3-5,7-8,12,14-15,18,24-26H,6H2,1-2H3,(H,19,20,22)/t12-,14-,15-,18?/m1/s1

Standard InChI Key:  APQIAUXRPNCQAC-PZGKNFOESA-N

Molfile:  

     RDKit          2D

 27 30  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
    4.1292   -4.0792    0.0000 C   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   -3.4792    0.0000 N   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
    3.6042   -3.1917    0.0000 C   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
    3.6042   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875   -2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -7.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1000   -3.4917    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
    2.5667   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750   -3.2042    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
    3.2292   -6.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -2.3042    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  4  2  0
 10  6  1  0
 11  8  1  0
 12  9  1  0
 13  3  2  0
 14 16  2  0
 15 12  1  0
 16 13  1  0
 17 15  2  0
 18 17  1  0
  6 19  1  6
 20 15  1  0
 10 21  1  6
 22 23  1  0
 23 20  2  0
 11 24  1  1
 25 24  1  0
 26 17  1  0
 27 22  1  0
  4  5  1  0
 10 11  1  0
 14  9  1  0
 22 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA610811

   (3R,4S,5R)-2-[6-(2,4-dimethylanilino)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: 371.40

Molecular Weight (Monoisotopic): 371.1594

AlogP: 0.80

#Rotatable Bonds: 4

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: 2.59

CX LogP: 1.20

CX LogD: 1.20

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: 0.06

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