2-(Allylthio)adenosine-5'-O-[(phosphonomethyl)phosphonic Acid]

ID: ALA4472826

Chembl Id: CHEMBL4472826

PubChem CID: 155535967

Max Phase: Preclinical

Molecular Formula: C14H21N5O9P2S

Molecular Weight: 497.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CCSc1nc(N)c2ncn([C@@H]3O[C@H](COP(=O)(O)CP(=O)(O)O)[C@@H](O)[C@H]3O)c2n1

Standard InChI:  InChI=1S/C14H21N5O9P2S/c1-2-3-31-14-17-11(15)8-12(18-14)19(5-16-8)13-10(21)9(20)7(28-13)4-27-30(25,26)6-29(22,23)24/h2,5,7,9-10,13,20-21H,1,3-4,6H2,(H,25,26)(H2,15,17,18)(H2,22,23,24)/t7-,9-,10-,13-/m1/s1

Standard InChI Key:  SAWBMJODLSSAGJ-QYVSTXNMSA-N

Alternative Forms

1. Parent:

   

   ALA4472826

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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: 497.36

Molecular Weight (Monoisotopic): 497.0535

AlogP: -0.36

#Rotatable Bonds: 9

Polar Surface Area: 223.37

Molecular Species: ACID

HBA: 12

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.98

CX Basic pKa: 5.07

CX LogP: -3.89

CX LogD: -6.22

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.11

Np Likeness Score: 0.42

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