[[(2R,3S,4R,5R)-5-(6-anilinopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]phosphono hydrogen phosphate

ID: ALA5202979

Chembl Id: CHEMBL5202979

PubChem CID: 44755145

Max Phase: Preclinical

Molecular Formula: C16H20N5O13P3

Molecular Weight: 583.28

Names and Identifiers

Canonical SMILES:  O=P(O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(Nc4ccccc4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H20N5O13P3/c22-12-10(6-31-36(27,28)34-37(29,30)33-35(24,25)26)32-16(13(12)23)21-8-19-11-14(17-7-18-15(11)21)20-9-4-2-1-3-5-9/h1-5,7-8,10,12-13,16,22-23H,6H2,(H,27,28)(H,29,30)(H,17,18,20)(H2,24,25,26)/t10-,12-,13-,16-/m1/s1

Standard InChI Key:  MXSCITZYHDRLLP-XNIJJKJLSA-N

Alternative Forms

1. Parent:

   

   ALA5202979

   [[(2R,3S,4R,5R)-5-(6-anilinopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 583.28

Molecular Weight (Monoisotopic): 583.0270

AlogP: 0.53

#Rotatable Bonds: 10

Polar Surface Area: 265.14

Molecular Species: ACID

HBA: 14

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.89

CX Basic pKa: 3.59

CX LogP: -2.51

CX LogD: -8.20

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.16

Np Likeness Score: 0.75

References

1. Isaak A, Dobelmann C, Füsser FT, Erlitz KS, Koch O, Junker A..  (2022)  Unveiling the Structure-Activity Relationships at the Orthosteric Binding Site of P2X Ion Channels: The Route to Selectivity.,  65  (16.0): [PMID:35930402] [10.1021/acs.jmedchem.2c00812]

Source

Source(1):

• Scientific Literature