[({[(2S,3S,4R,5R)-5-(6-Chloro-4-{[(2-chlorophenyl)methyl]-amino}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)methyl]phosphonic Acid

ID: ALA4782125

PubChem CID: 148018940

Max Phase: Preclinical

Molecular Formula: C18H20Cl2N5O6PS

Molecular Weight: 536.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=P(O)(O)CSC[C@H]1O[C@@H](n2ncc3c(NCc4ccccc4Cl)nc(Cl)nc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C18H20Cl2N5O6PS/c19-11-4-2-1-3-9(11)5-21-15-10-6-22-25(16(10)24-18(20)23-15)17-14(27)13(26)12(31-17)7-33-8-32(28,29)30/h1-4,6,12-14,17,26-27H,5,7-8H2,(H,21,23,24)(H2,28,29,30)/t12-,13-,14-,17-/m1/s1

Standard InChI Key:  JAIAGXYPLMOWIL-VMUDFCTBSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    6.4921  -10.2273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9143   -9.6495    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.7028  -10.4388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008   -9.3606    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9097   -8.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3543   -8.5840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6911   -9.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9416   -9.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7629   -9.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0176   -9.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2472  -10.5087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4615  -10.5087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0495   -6.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6409   -7.3231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0495   -8.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8708   -8.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2794   -7.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8708   -6.6140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1255   -8.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4581   -9.2937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7948   -8.8136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1009   -7.3230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5093   -6.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6409   -5.9008    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.3265   -6.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7324   -7.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5489   -7.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9576   -6.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5440   -5.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7289   -5.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3166   -5.2017    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5239   -9.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1391   -9.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  6 10  1  0
  9 11  1  6
  8 12  1  6
  7  5  1  1
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 19 20  2  0
 20 21  1  0
 15 21  1  0
 16 19  1  0
 22 23  1  0
 17 22  1  0
 13 24  1  0
 10 21  1  1
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 30 31  1  0
  4 32  1  0
 32  2  1  0
  2 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4782125

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 536.33

Molecular Weight (Monoisotopic): 535.0249

AlogP: 2.23

#Rotatable Bonds: 8

Polar Surface Area: 162.85

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.63

CX Basic pKa: 1.12

CX LogP: 0.58

CX LogD: -1.21

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.21

Np Likeness Score: -0.74

References

1. Du X,Moore J,Blank BR,Eksterowicz J,Sutimantanapi D,Yuen N,Metzger T,Chan B,Huang T,Chen X,Chen Y,Duong F,Kong W,Chang JH,Sun J,Zavorotinskaya T,Ye Q,Junttila MR,Ndubaku C,Friedman LS,Fantin VR,Sun D.  (2020)  Orally Bioavailable Small-Molecule CD73 Inhibitor (OP-5244) Reverses Immunosuppression through Blockade of Adenosine Production.,  63  (18): [PMID:32865411] [10.1021/acs.jmedchem.0c01086]

Source

Source(1):

• Scientific Literature