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

ID: ALA609814

PubChem CID: 46876028

Max Phase: Preclinical

Molecular Formula: C12H16N4O4S

Molecular Weight: 312.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCSc1ncnc2c1cnn2C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C12H16N4O4S/c1-2-21-11-6-3-15-16(10(6)13-5-14-11)12-9(19)8(18)7(4-17)20-12/h3,5,7-9,12,17-19H,2,4H2,1H3/t7-,8-,9-,12?/m1/s1

Standard InChI Key:  DFGSVBXISOKGEU-RNRLFLAJSA-N

Molfile:  

     RDKit          2D

 21 23  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
    7.5417   -8.2917    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
    6.8417   -6.8542    0.0000 O   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
    6.3042   -4.1667    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
    5.5417   -5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0542   -9.1250    0.0000 O   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
    5.6042   -9.1250    0.0000 O   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
    7.0625   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0542   -1.9542    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  2  1  0
  6  3  1  0
  7  2  1  0
  8  5  1  0
  9  4  2  0
 10  7  1  0
 11  3  2  0
 12  6  2  0
 13 14  2  0
 14 11  1  0
  5 15  1  6
 16 12  1  0
  8 17  1  6
 10 18  1  1
 19 18  1  0
 20 16  1  0
 21 20  1  0
  9  6  1  0
 10  8  1  0
 12 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA609814

   (3R,4S,5R)-2-(4-ethylsulfanylpyrazolo[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: 312.35

Molecular Weight (Monoisotopic): 312.0892

AlogP: -0.45

#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: 2.19

CX LogP: -0.44

CX LogD: -0.44

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: -0.35

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