{[{[(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]methoxy}(methoxy)phosphoryl]methyl}phosphonic Acid

ID: ALA4790529

PubChem CID: 142470829

Max Phase: Preclinical

Molecular Formula: C19H23Cl2N5O9P2

Molecular Weight: 598.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COP(=O)(CP(=O)(O)O)OC[C@H]1O[C@@H](n2ncc3c(NCc4ccccc4Cl)nc(Cl)nc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H23Cl2N5O9P2/c1-33-37(32,9-36(29,30)31)34-8-13-14(27)15(28)18(35-13)26-17-11(7-23-26)16(24-19(21)25-17)22-6-10-4-2-3-5-12(10)20/h2-5,7,13-15,18,27-28H,6,8-9H2,1H3,(H,22,24,25)(H2,29,30,31)/t13-,14-,15-,18-,37?/m1/s1

Standard InChI Key:  GKEUAVPYIGQALX-UBTKDOLISA-N

Molfile:  

 
     RDKit          2D

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    4.8371   -7.7674    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.2455   -7.0551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8684   -7.4785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4504   -8.0605    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.6634   -7.2655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6151   -8.0244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3337   -7.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5633   -9.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7776   -9.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3656   -6.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1109   -7.4763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4170   -5.9858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8254   -5.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9570   -4.5636    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2302   -8.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.0485   -5.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8650   -5.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2737   -5.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8600   -4.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0450   -4.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6327   -3.8645    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0627   -7.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  1  0
  9 10  1  0
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  9 13  1  0
 12 14  1  6
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 10  8  1  1
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 22 23  2  0
 23 24  1  0
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  7  2  1  0
  2 28  1  0
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  5 29  2  0
 26 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 35 36  1  0
  3 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790529

   ---

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: 598.27

Molecular Weight (Monoisotopic): 597.0348

AlogP: 2.36

#Rotatable Bonds: 10

Polar Surface Area: 198.38

Molecular Species: ACID

HBA: 12

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.57

CX Basic pKa: 1.10

CX LogP: -0.09

CX LogD: -1.90

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.17

Np Likeness Score: -0.48

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