2-(4-Cyclopentylsulfanyl-pyrazolo[3,4-d]pyrimidin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA610687

PubChem CID: 46875968

Max Phase: Preclinical

Molecular Formula: C15H20N4O4S

Molecular Weight: 352.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1OC(n2ncc3c(SC4CCCC4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H20N4O4S/c20-6-10-11(21)12(22)15(23-10)19-13-9(5-18-19)14(17-7-16-13)24-8-3-1-2-4-8/h5,7-8,10-12,15,20-22H,1-4,6H2/t10-,11-,12-,15?/m1/s1

Standard InChI Key:  AMOBMTCLNADFRE-IUUYLUPUSA-N

Molfile:  

     RDKit          2D

 24 27  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
    7.9750   -7.4125    0.0000 C   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
    8.4417   -5.0417    0.0000 N   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
    7.5417   -8.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417   -6.8542    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
    6.1292   -8.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -7.4125    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
    5.5417   -4.6125    0.0000 N   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
    5.5417   -5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0500   -9.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6125   -9.1125    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
    4.8667   -7.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -7.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8667   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0125   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4542   -2.5250    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  3  1  0
  6  2  1  0
  7  2  1  0
  8  5  2  0
  9  6  1  0
 10  4  2  0
 11  7  1  0
 12  3  2  0
 13 15  2  0
 14  8  1  0
 15 12  1  0
  6 16  1  6
  9 17  1  6
 18 14  1  0
 11 19  1  1
 20 19  1  0
 21 18  1  0
 22 18  1  0
 23 22  1  0
 24 21  1  0
  5 10  1  0
  9 11  1  0
 13  8  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA610687

   (3R,4S,5R)-2-(4-cyclopentylsulfanylpyrazolo[3,4-d]pyrimidin-1-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: 352.42

Molecular Weight (Monoisotopic): 352.1205

AlogP: 0.47

#Rotatable Bonds: 4

Polar Surface Area: 113.52

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.42

CX Basic pKa: 2.15

CX LogP: 0.45

CX LogD: 0.45

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.68

Np Likeness Score: -0.14

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