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

ID: ALA4756805

PubChem CID: 152945183

Max Phase: Preclinical

Molecular Formula: C20H32ClN6O9PS

Molecular Weight: 599.00

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H32ClN6O9PS/c1-20(37(30,31)32,10-26(2)38(3,33)34)35-9-13-14(28)15(29)18(36-13)27-17-12(8-22-27)16(24-19(21)25-17)23-11-6-4-5-7-11/h8,11,13-15,18,28-29H,4-7,9-10H2,1-3H3,(H,23,24,25)(H2,30,31,32)/t13-,14-,15-,18-,20?/m1/s1

Standard InChI Key:  UNPLFAQHIDLLKM-FSXPKSEBSA-N

Molfile:  

 
     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA4756805

   ---

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: 599.00

Molecular Weight (Monoisotopic): 598.1378

AlogP: 0.26

#Rotatable Bonds: 10

Polar Surface Area: 209.46

Molecular Species: ACID

HBA: 12

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.22

CX Basic pKa: 0.80

CX LogP: -1.45

CX LogD: -3.21

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.18

Np Likeness Score: -0.54

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