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

ID: ALA4536899

Chembl Id: CHEMBL4536899

PubChem CID: 155548570

Max Phase: Preclinical

Molecular Formula: C19H31N5O9P2S

Molecular Weight: 567.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc(SCCC2CCCCC2)nc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)CP(=O)(O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C19H31N5O9P2S/c20-16-13-17(23-19(22-16)36-7-6-11-4-2-1-3-5-11)24(9-21-13)18-15(26)14(25)12(33-18)8-32-35(30,31)10-34(27,28)29/h9,11-12,14-15,18,25-26H,1-8,10H2,(H,30,31)(H2,20,22,23)(H2,27,28,29)/t12-,14-,15-,18-/m1/s1

Standard InChI Key:  XPXPQQYUCVQSPM-SCFUHWHPSA-N

Alternative Forms

1. Parent:

   

   ALA4536899

   ---

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: 567.50

Molecular Weight (Monoisotopic): 567.1318

AlogP: 1.43

#Rotatable Bonds: 10

Polar Surface Area: 223.37

Molecular Species: ACID

HBA: 12

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.98

CX Basic pKa: 5.12

CX LogP: -2.26

CX LogD: -4.59

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.14

Np Likeness Score: 0.36

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