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

ID: ALA605216

PubChem CID: 135976310

Max Phase: Preclinical

Molecular Formula: C11H15N5O6

Molecular Weight: 313.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nc2c(O)nc(N)nc2n1C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H15N5O6/c1-21-11-13-4-7(14-10(12)15-8(4)20)16(11)9-6(19)5(18)3(2-17)22-9/h3,5-6,9,17-19H,2H2,1H3,(H3,12,14,15,20)/t3-,5-,6-,9?/m1/s1

Standard InChI Key:  MWVSREMEETTXDC-LZGMGDPASA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    5.2042   -3.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -2.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -3.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2250   -5.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -2.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -4.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -2.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000   -5.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -2.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -6.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -3.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -1.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -6.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -4.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -5.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9250   -3.6375    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
 14 20  1  1
 21 20  1  0
 22 15  1  0
  6  5  1  0
 14 13  1  0
 11  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA605216

   ---

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: 313.27

Molecular Weight (Monoisotopic): 313.1022

AlogP: -2.27

#Rotatable Bonds: 3

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: -1.19

CX LogD: -1.19

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.42

Np Likeness Score: 0.71

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