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

ID: ALA4475460

Chembl Id: CHEMBL4475460

Cas Number: 35057-44-4

PubChem CID: 193201

Max Phase: Preclinical

Molecular Formula: C11H16ClN5O9P2

Molecular Weight: 459.68

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H16ClN5O9P2/c12-11-15-8(13)5-9(16-11)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:  INCBEFXULMHULH-KQYNXXCUSA-N

Alternative Forms

1. Parent:

   

   ALA4475460

   2-Chloro-5'-adenylyl methylenediphosphonate

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: 0.95

CX Basic pKa: 2.32

CX LogP: -4.08

CX LogD: -7.26

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.23

Np Likeness Score: 0.79

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. Lawson KV,Kalisiak J,Lindsey EA,Newcomb ET,Leleti MR,Debien L,Rosen BR,Miles DH,Sharif EU,Jeffrey JL,Tan JBL,Chen A,Zhao S,Xu G,Fu L,Jin L,Park TW,Berry W,Moschütz S,Scaletti E,Sträter N,Walker NP,Young SW,Walters MJ,Schindler U,Powers JP.  (2020)  Discovery of AB680: A Potent and Selective Inhibitor of CD73.,  63  (20.0): [PMID:32614585] [10.1021/acs.jmedchem.0c00525]

Source

Source(1):

• Scientific Literature