{2-[1-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylsulfanyl]-ethyl}-phosphonic acid diethyl ester

ID: ALA611574

PubChem CID: 46876055

Max Phase: Preclinical

Molecular Formula: C16H25N4O7PS

Molecular Weight: 448.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H25N4O7PS/c1-3-25-28(24,26-4-2)5-6-29-15-10-7-19-20(14(10)17-9-18-15)16-13(23)12(22)11(8-21)27-16/h7,9,11-13,16,21-23H,3-6,8H2,1-2H3/t11-,12-,13-,16?/m1/s1

Standard InChI Key:  UDCIMFURNLEWIJ-QMCPWEQMSA-N

Molfile:  

     RDKit          2D

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    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
    7.8167   -1.5042    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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    5.6167   -9.1042    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
    6.2917   -0.6167    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
    6.2917    0.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5667    0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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 15 12  1  0
 16 23  1  0
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  5 18  1  6
 19 13  1  0
 20  9  1  0
 21  9  1  0
  8 22  1  6
 23 19  1  0
 11 24  1  1
 25 24  1  0
 26 20  1  0
 27 21  1  0
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 29 27  1  0
  6 10  1  0
  8 11  1  0
 14 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA611574

   (3R,4S,5R)-2-[4-(2-diethoxyphosphorylethylsulfanyl)pyrazolo[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: 448.44

Molecular Weight (Monoisotopic): 448.1182

AlogP: 0.80

#Rotatable Bonds: 10

Polar Surface Area: 149.05

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.42

CX Basic pKa: 2.18

CX LogP: -0.75

CX LogD: -0.75

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.27

Np Likeness Score: -0.22

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