2-Amino-8-benzyloxy-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one

ID: ALA603769

PubChem CID: 135976319

Max Phase: Preclinical

Molecular Formula: C17H19N5O6

Molecular Weight: 389.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2nc(OCc3ccccc3)n(C3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1

Standard InChI:  InChI=1S/C17H19N5O6/c18-16-20-13-10(14(26)21-16)19-17(27-7-8-4-2-1-3-5-8)22(13)15-12(25)11(24)9(6-23)28-15/h1-5,9,11-12,15,23-25H,6-7H2,(H3,18,20,21,26)/t9-,11-,12-,15?/m1/s1

Standard InChI Key:  RNSGUQLXDMZREX-FJFSNTMWSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.5167    0.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750    0.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750    1.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292    1.5458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917    0.0833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    1.2458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -0.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917    1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    0.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917    0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -2.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3500    0.4708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917    2.4208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -2.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042    0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292    0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -0.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417    0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2625    0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792    0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  2  1  0
  6  3  2  0
  7  2  2  0
  8  4  1  0
  9 12  2  0
 10  4  1  0
 11  5  2  0
 12  7  1  0
 13  8  1  0
 14 10  1  0
 15  3  1  0
  8 16  1  6
 17 12  1  0
 18 11  1  0
 13 19  1  6
 20 15  1  0
 14 21  1  1
 22 20  1  0
 23 21  1  0
 24 22  2  0
 25 22  1  0
 26 25  2  0
 27 24  1  0
 28 26  1  0
  6  5  1  0
 14 13  1  0
 11  9  1  0
 27 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA603769

   ---

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: 389.37

Molecular Weight (Monoisotopic): 389.1335

AlogP: -0.70

#Rotatable Bonds: 5

Polar Surface Area: 169.00

Molecular Species: NEUTRAL

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.34

CX Basic pKa: ┄

CX LogP: 0.54

CX LogD: 0.54

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.38

Np Likeness Score: 0.39

References

1. Lin TS, Cheng JC, Ishiguro K, Sartorelli AC..  (1985)  8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells.,  28  (9): [PMID:3861870] [10.1021/jm00147a012]

Source

Source(1):

• Scientific Literature