[1-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylsulfanyl]-acetic acid methyl ester

ID: ALA609815

PubChem CID: 46876029

Max Phase: Preclinical

Molecular Formula: C13H16N4O6S

Molecular Weight: 356.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CSc1ncnc2c1cnn2C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C13H16N4O6S/c1-22-8(19)4-24-12-6-2-16-17(11(6)14-5-15-12)13-10(21)9(20)7(3-18)23-13/h2,5,7,9-10,13,18,20-21H,3-4H2,1H3/t7-,9-,10-,13?/m1/s1

Standard InChI Key:  SEFFYQFTWCTCGT-RJNFYWFKSA-N

Molfile:  

     RDKit          2D

 24 26  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   -4.1667    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
    7.0542   -1.9542    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
    6.2917   -1.5167    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
    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
    7.8167   -1.5042    0.0000 O   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
    8.5875   -1.9417    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  6  2  0
 12  3  2  0
 13 15  2  0
 14 11  1  0
 15 12  1  0
 16 19  1  0
  5 17  1  6
 18 16  2  0
 19 14  1  0
  8 20  1  6
 10 21  1  1
 22 16  1  0
 23 21  1  0
 24 22  1  0
  6  9  1  0
  8 10  1  0
 13 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA609815

   methyl 2-[1-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrazolo[3,4-d]pyrimidin-4-yl]sulfanylacetate

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: 356.36

Molecular Weight (Monoisotopic): 356.0791

AlogP: -1.30

#Rotatable Bonds: 5

Polar Surface Area: 139.82

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.42

CX Basic pKa: 2.05

CX LogP: -1.38

CX LogD: -1.38

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.34

Np Likeness Score: -0.28

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