2-(6-Amino-purin-9-yl)-5-methylsulfanyl-tetrahydro-furan-3,4-diol

ID: ALA603356

PubChem CID: 46874156

Max Phase: Preclinical

Molecular Formula: C10H13N5O3S

Molecular Weight: 283.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS[C@H]1OC(n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C10H13N5O3S/c1-19-10-6(17)5(16)9(18-10)15-3-14-4-7(11)12-2-13-8(4)15/h2-3,5-6,9-10,16-17H,1H3,(H2,11,12,13)/t5-,6+,9?,10-/m1/s1

Standard InChI Key:  XLWLKFPELPQJBD-MNXVAAOTSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    3.0541   -4.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8791   -4.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1359   -3.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4666   -3.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016   -3.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5683   -5.3502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3633   -5.3514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0169   -3.6446    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4040   -4.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750   -2.6875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0833   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0833   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750   -1.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8875   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -2.8000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1583   -1.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1583   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -1.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  1  1  0
  1  2  1  0
  1  6  1  6
  2  7  1  6
  2  3  1  0
  5  8  1  1
  3  4  1  0
  8  9  1  0
 11 10  1  0
 12 11  2  0
 13 14  2  0
 14 10  1  0
 15 12  1  0
 16 11  1  0
 17 18  1  0
 18 16  2  0
 19 15  1  0
 12 13  1  0
 15 17  2  0
  3 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA603356

   (3R,4S,5R)-2-(6-aminopurin-9-yl)-5-methylsulfanyloxolane-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: 283.31

Molecular Weight (Monoisotopic): 283.0739

AlogP: -0.65

#Rotatable Bonds: 2

Polar Surface Area: 119.31

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.36

CX Basic pKa: 3.94

CX LogP: -0.47

CX LogD: -0.47

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.66

Np Likeness Score: 0.62

References

1. Jacobson KA, Siddiqi SM, Olah ME, Ji XD, Melman N, Bellamkonda K, Meshulam Y, Stiles GL, Kim HO..  (1995)  Structure-activity relationships of 9-alkyladenine and ribose-modified adenosine derivatives at rat A3 adenosine receptors.,  38  (10): [PMID:7752196] [10.1021/jm00010a017]

Source

Source(1):

• Scientific Literature