S-Allylthio-6-mercaptopurine

ID: ALA444696

PubChem CID: 24896592

Max Phase: Preclinical

Molecular Formula: C8H8N4S2

Molecular Weight: 224.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCSSc1ncnc2nc[nH]c12

Standard InChI:  InChI=1S/C8H8N4S2/c1-2-3-13-14-8-6-7(10-4-9-6)11-5-12-8/h2,4-5H,1,3H2,(H,9,10,11,12)

Standard InChI Key:  HSQBKWFKQCEING-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
    2.7569   -0.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7557   -1.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4706   -2.1652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4688   -0.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1841   -0.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1844   -1.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705   -2.0029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4561   -1.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9701   -0.6658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4663    0.3128    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1795    0.7274    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1771    1.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8903    1.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8878    2.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  5  4  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  4  1  1  0
  4 10  1  0
  5  6  1  0
 10 11  1  0
 11 12  1  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA444696

   S-Allylthio-6-mercaptopurine

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: 224.31

Molecular Weight (Monoisotopic): 224.0190

AlogP: 2.28

#Rotatable Bonds: 4

Polar Surface Area: 54.46

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.63

CX Basic pKa: 2.15

CX LogP: 1.95

CX LogD: 1.93

Aromatic Rings: 2

Heavy Atoms: 14

QED Weighted: 0.37

Np Likeness Score: -0.31

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