({(2R,3S,4R,5R)-5-[6-Chloro-4-(cyclopentylamino)-1H-pyrazolo-[3,4-d]pyrimidin-1-yl]-3,4-dihydroxyoxolan-2-yl}methoxy)-(phosphono)acetic Acid

ID: ALA4781819

PubChem CID: 156064944

Max Phase: Preclinical

Molecular Formula: C17H23ClN5O9P

Molecular Weight: 507.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)C(OC[C@H]1O[C@@H](n2ncc3c(NC4CCCC4)nc(Cl)nc32)[C@H](O)[C@@H]1O)P(=O)(O)O

Standard InChI:  InChI=1S/C17H23ClN5O9P/c18-17-21-12(20-7-3-1-2-4-7)8-5-19-23(13(8)22-17)14-11(25)10(24)9(32-14)6-31-16(15(26)27)33(28,29)30/h5,7,9-11,14,16,24-25H,1-4,6H2,(H,26,27)(H,20,21,22)(H2,28,29,30)/t9-,10-,11-,14-,16?/m1/s1

Standard InChI Key:  PTRPYXPJAKIGAI-BHCDIJIXSA-N

Molfile:  

 
     RDKit          2D

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    5.2086   -8.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308   -7.8913    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.4193   -8.6806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6220   -7.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0667   -6.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4034   -7.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6539   -8.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4752   -8.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7299   -7.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9595   -8.7381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1738   -8.7381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7618   -4.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3532   -5.5525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7618   -6.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5831   -6.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5831   -4.8434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8378   -7.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1704   -7.5231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5071   -7.0430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8132   -5.5524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2216   -4.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3532   -4.1302    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0169   -7.5921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2387   -7.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8554   -7.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0340   -4.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2033   -3.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4943   -3.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8869   -4.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0668   -6.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6727   -5.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890   -6.2931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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  6  7  1  0
  7  8  1  0
  8  9  1  0
  5  9  1  0
  8 10  1  6
  7 11  1  6
  6  4  1  1
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 18 19  2  0
 19 20  1  0
 14 20  1  0
 15 18  1  0
 21 22  1  0
 16 21  1  0
 12 23  1  0
  9 20  1  1
  4 24  1  0
 24 25  1  0
 25  2  1  0
  2 26  2  0
 22 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 22  1  0
 25 31  1  0
 31 32  2  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781819

   ---

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: 507.82

Molecular Weight (Monoisotopic): 507.0922

AlogP: 0.06

#Rotatable Bonds: 8

Polar Surface Area: 209.38

Molecular Species: ACID

HBA: 11

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.11

CX Basic pKa: 0.76

CX LogP: -1.33

CX LogD: -6.50

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.21

Np Likeness Score: -0.20

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