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

ID: ALA4790457

PubChem CID: 162669757

Max Phase: Preclinical

Molecular Formula: C19H22Cl2N5O7P

Molecular Weight: 534.29

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H22Cl2N5O7P/c20-12-4-2-1-3-10(12)7-22-16-11-8-23-26(17(11)25-19(21)24-16)18-15(28)14(27)13(33-18)5-6-32-9-34(29,30)31/h1-4,8,13-15,18,27-28H,5-7,9H2,(H,22,24,25)(H2,29,30,31)/t13-,14-,15-,18-/m1/s1

Standard InChI Key:  QHXUEAYQJHERGY-ATNYBXOESA-N

Molfile:  

 
     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    5.1219  -10.7473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1260   -9.9301    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162  -10.3351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2908   -9.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9015   -9.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3461   -9.1164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6828   -9.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9334  -10.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7547  -10.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0094   -9.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2390  -11.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4532  -11.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0413   -7.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6327   -7.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0413   -8.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8626   -8.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2712   -7.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8626   -7.1464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1172   -9.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4499   -9.8261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7866   -9.3460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0927   -7.8554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5011   -7.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6327   -6.4332    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.3183   -7.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7242   -7.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5406   -7.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9494   -7.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5357   -6.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7206   -6.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3084   -5.7341    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5140   -9.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9058  -10.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9604   -9.1327    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 33  1  0
 33  2  1  0
  2 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790457

   ---

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: 534.29

Molecular Weight (Monoisotopic): 533.0634

AlogP: 1.91

#Rotatable Bonds: 9

Polar Surface Area: 172.08

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.35

CX Basic pKa: 1.01

CX LogP: 0.14

CX LogD: -1.65

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.15

Np Likeness Score: -0.47

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