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

ID: ALA611884

PubChem CID: 46875987

Max Phase: Preclinical

Molecular Formula: C12H16N4O4S2

Molecular Weight: 344.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1nc(SC)c2ncn(C3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1

Standard InChI:  InChI=1S/C12H16N4O4S2/c1-21-10-6-9(14-12(15-10)22-2)16(4-13-6)11-8(19)7(18)5(3-17)20-11/h4-5,7-8,11,17-19H,3H2,1-2H3/t5-,7-,8-,11?/m1/s1

Standard InChI Key:  FTGZLZPNEHEUMH-YNJARDAQSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    7.9250   -5.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792   -5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9417   -7.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750   -4.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3042   -5.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -4.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -8.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4417   -5.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -4.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8125   -6.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3042   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -8.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6750   -7.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3042   -3.2875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -5.9375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0375   -9.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5792   -9.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -7.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -7.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0625   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -5.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  2  2  0
  6  8  2  0
  7  3  1  0
  8  1  1  0
  9 12  2  0
 10  3  1  0
 11  4  2  0
 12  5  1  0
 13  7  1  0
 14 10  1  0
 15 11  1  0
 16 12  1  0
  7 17  1  6
 13 18  1  6
 14 19  1  1
 20 19  1  0
 21 15  1  0
 22 16  1  0
  6  4  1  0
 14 13  1  0
 11  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA611884

   (3R,4S,5R)-2-[2,6-bis(methylsulfanyl)purin-9-yl]-5-(hydroxymethyl)oxolane-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: 344.42

Molecular Weight (Monoisotopic): 344.0613

AlogP: -0.12

#Rotatable Bonds: 4

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: 2.05

CX LogP: 0.67

CX LogD: 0.67

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.40

Np Likeness Score: 0.31

References

1. Krenitsky TA, Rideout JL, Koszalka GW, Inmon RB, Chao EY, Elion GB, Latter VS, Williams RB..  (1982)  Pyrazolo[3,4-d]pyrimidine ribonucleosides as anticoccidials. 1. Synthesis and activity of some nucleosides of purines and 4-(alkylthio)pyrazolo[3,4-d]pyrimidines.,  25  (1): [PMID:7086819] [10.1021/jm00343a007]

Source

Source(1):

• Scientific Literature