[[(2R,3S,4R,5R)-5-[6-[benzyl(methyl)amino]-2-chloropurin-9-yl]-3,4-dihydroxytetrahydrofuran-2-yl]methoxyhydroxyphosphoryl]methylphosphonic acid

ID: ALA4452072

Chembl Id: CHEMBL4452072

PubChem CID: 146676950

Max Phase: Preclinical

Molecular Formula: C19H24ClN5O9P2

Molecular Weight: 563.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(Cc1ccccc1)c1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)CP(=O)(O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C19H24ClN5O9P2/c1-24(7-11-5-3-2-4-6-11)16-13-17(23-19(20)22-16)25(9-21-13)18-15(27)14(26)12(34-18)8-33-36(31,32)10-35(28,29)30/h2-6,9,12,14-15,18,26-27H,7-8,10H2,1H3,(H,31,32)(H2,28,29,30)/t12-,14-,15-,18-/m1/s1

Standard InChI Key:  NRCRRUYZIFHEBT-SCFUHWHPSA-N

Alternative Forms

1. Parent:

   

   ALA4452072

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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: 563.83

Molecular Weight (Monoisotopic): 563.0738

AlogP: 1.07

#Rotatable Bonds: 9

Polar Surface Area: 200.59

Molecular Species: ACID

HBA: 11

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.92

CX Basic pKa: 2.14

CX LogP: -1.08

CX LogD: -4.55

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.18

Np Likeness Score: 0.19

References

1. Bhattarai S, Pippel J, Scaletti E, Idris R, Freundlieb M, Rolshoven G, Renn C, Lee SY, Abdelrahman A, Zimmermann H, El-Tayeb A, Müller CE, Sträter N..  (2020)  2-Substituted α,β-Methylene-ADP Derivatives: Potent Competitive Ecto-5'-nucleotidase (CD73) Inhibitors with Variable Binding Modes.,  63  (6): [PMID:32045236] [10.1021/acs.jmedchem.9b01611]

2. 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]

3. Schmies CC,Rolshoven G,Idris RM,Losenkova K,Renn C,Schäkel L,Al-Hroub H,Wang Y,Garofano F,Schmidt-Wolf IGH,Zimmermann H,Yegutkin GG,Müller CE.  (2020)  Fluorescent Probes for Ecto-5'-nucleotidase (CD73).,  11  (11): [PMID:33214837] [10.1021/acsmedchemlett.0c00391]

Source

Source(1):

• Scientific Literature