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

ID: ALA606018

PubChem CID: 135976378

Max Phase: Preclinical

Molecular Formula: C11H15N5O5S

Molecular Weight: 329.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1nc2c(O)nc(N)nc2n1C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H15N5O5S/c1-22-11-13-4-7(14-10(12)15-8(4)20)16(11)9-6(19)5(18)3(2-17)21-9/h3,5-6,9,17-19H,2H2,1H3,(H3,12,14,15,20)/t3-,5-,6-,9?/m1/s1

Standard InChI Key:  VEABMYFEYLXTSD-LZGMGDPASA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    3.2667   -0.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750    0.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625   -0.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042    0.4958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167   -1.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5250    0.1208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -2.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -0.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625    1.6583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750   -3.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -0.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -0.5792    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:

   

   ALA606018

   ---

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: 329.34

Molecular Weight (Monoisotopic): 329.0794

AlogP: -1.55

#Rotatable Bonds: 3

Polar Surface Area: 159.77

Molecular Species: NEUTRAL

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.43

CX Basic pKa: 0.11

CX LogP: -0.40

CX LogD: -0.40

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.42

Np Likeness Score: 0.28

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