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

ID: ALA610688

PubChem CID: 46875969

Max Phase: Preclinical

Molecular Formula: C15H22N4O4S

Molecular Weight: 354.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCSc1ncnc2c1cnn2C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H22N4O4S/c1-2-3-4-5-24-14-9-6-18-19(13(9)16-8-17-14)15-12(22)11(21)10(7-20)23-15/h6,8,10-12,15,20-22H,2-5,7H2,1H3/t10-,11-,12-,15?/m1/s1

Standard InChI Key:  LILYXUUSSMBXLP-IUUYLUPUSA-N

Molfile:  

     RDKit          2D

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    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   -9.1125    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   -9.1167    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
    7.8125   -0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8167   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5750   -0.1792    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
 22 23  1  0
 23 21  1  0
 24 22  1  0
  6  9  1  0
  8 10  1  0
 13 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA610688

   (2R,3S,4R)-2-(hydroxymethyl)-5-(4-pentylsulfanylpyrazolo[3,4-d]pyrimidin-1-yl)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: 354.43

Molecular Weight (Monoisotopic): 354.1362

AlogP: 0.72

#Rotatable Bonds: 7

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: 0.97

CX LogD: 0.97

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.38

Np Likeness Score: -0.25

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