2-(1-Piperazinyl)adenosine-5'-O-[(phosphonomethyl)phosphonic Acid]

ID: ALA4569080

Chembl Id: CHEMBL4569080

PubChem CID: 145925614

Max Phase: Preclinical

Molecular Formula: C15H25N7O9P2

Molecular Weight: 509.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc(N2CCNCC2)nc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)CP(=O)(O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H25N7O9P2/c16-12-9-13(20-15(19-12)21-3-1-17-2-4-21)22(6-18-9)14-11(24)10(23)8(31-14)5-30-33(28,29)7-32(25,26)27/h6,8,10-11,14,17,23-24H,1-5,7H2,(H,28,29)(H2,16,19,20)(H2,25,26,27)/t8-,10-,11-,14-/m1/s1

Standard InChI Key:  GUHCLCYLXMLIOC-IDTAVKCVSA-N

Alternative Forms

1. Parent:

   

   ALA4569080

   ---

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: 509.35

Molecular Weight (Monoisotopic): 509.1189

AlogP: -2.23

#Rotatable Bonds: 7

Polar Surface Area: 238.64

Molecular Species: ZWITTERION

HBA: 13

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.99

CX Basic pKa: 8.77

CX LogP: -7.23

CX LogD: -6.86

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.20

Np Likeness Score: 0.41

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