2-(6-Allyldisulfanyl-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol)

ID: ALA516889

PubChem CID: 25267117

Max Phase: Preclinical

Molecular Formula: C13H16N4O4S2

Molecular Weight: 356.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: S-Allylthio-6-mercaptopurine riboside | CHEMBL516889|SCHEMBL13425372|S-Allylthio-6-mercaptopurine riboside

Canonical SMILES:  C=CCSSc1ncnc2c1ncn2[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C13H16N4O4S2/c1-2-3-22-23-12-8-11(14-5-15-12)17(6-16-8)13-10(20)9(19)7(4-18)21-13/h2,5-7,9-10,13,18-20H,1,3-4H2/t7-,9-,10-,13-/m0/s1

Standard InChI Key:  UPMVDGSUFKTPMZ-PYSAPBNWSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    7.4152   -2.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4141   -3.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1289   -3.4777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1271   -1.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8425   -2.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8427   -3.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6288   -3.3154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1145   -2.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6284   -1.9783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1246   -0.9997    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8840   -4.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4034   -4.7696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8885   -5.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6731   -5.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6728   -4.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3402   -3.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3408   -5.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6338   -6.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8269   -6.3934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8379   -0.5851    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8354    0.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5486    0.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5462    1.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  7  1  6
 11 12  1  0
  2  3  1  0
  3  6  2  0
  1  2  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
  5  4  2  0
 15 16  1  1
  6  7  1  0
 14 17  1  1
  7  8  1  0
 13 18  1  6
  8  9  2  0
 18 19  1  0
  9  5  1  0
 10 20  1  0
  4  1  1  0
 20 21  1  0
  4 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA516889

   S-Allylthio-6-mercaptopurine riboside

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: 356.43

Molecular Weight (Monoisotopic): 356.0613

AlogP: 0.36

#Rotatable Bonds: 6

Polar Surface Area: 113.52

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 2.41

CX LogP: 0.43

CX LogD: 0.43

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.29

Np Likeness Score: 1.09

References

1. Miron T, Arditti F, Konstantinovski L, Rabinkov A, Mirelman D, Berrebi A, Wilchek M..  (2009)  Novel derivatives of 6-mercaptopurine: synthesis, characterization and antiproliferative activities of S-allylthio-mercaptopurines.,  44  (2): [PMID:18467007] [10.1016/j.ejmech.2008.03.027]

Source

Source(1):

• Scientific Literature