2-Amino-6-chloropurine Riboside-5'-O-[(phosphonomethyl)phosphonic Acid]

ID: ALA4456465

Chembl Id: CHEMBL4456465

PubChem CID: 155524529

Max Phase: Preclinical

Molecular Formula: C11H16ClN5O9P2

Molecular Weight: 459.68

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc(Cl)c2ncn([C@@H]3O[C@H](COP(=O)(O)CP(=O)(O)O)[C@@H](O)[C@H]3O)c2n1

Standard InChI:  InChI=1S/C11H16ClN5O9P2/c12-8-5-9(16-11(13)15-8)17(2-14-5)10-7(19)6(18)4(26-10)1-25-28(23,24)3-27(20,21)22/h2,4,6-7,10,18-19H,1,3H2,(H,23,24)(H2,13,15,16)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1

Standard InChI Key:  DESIWVJHLARCRX-KQYNXXCUSA-N

Alternative Forms

1. Parent:

   

   ALA4456465

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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: 459.68

Molecular Weight (Monoisotopic): 459.0112

AlogP: -0.98

#Rotatable Bonds: 6

Polar Surface Area: 223.37

Molecular Species: ACID

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.96

CX Basic pKa: 2.34

CX LogP: -4.11

CX LogD: -7.26

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.23

Np Likeness Score: 0.63

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]

Source

Source(1):

• Scientific Literature