(2R,3R,4S,5R)-2-(6-(benzyloxy)-9H-purin-9-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diol

ID: ALA259868

Chembl Id: CHEMBL259868

PubChem CID: 44451142

Max Phase: Preclinical

Molecular Formula: C17H18N4O5

Molecular Weight: 358.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c(OCc4ccccc4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C17H18N4O5/c22-6-11-13(23)14(24)17(26-11)21-9-20-12-15(21)18-8-19-16(12)25-7-10-4-2-1-3-5-10/h1-5,8-9,11,13-14,17,22-24H,6-7H2/t11-,13-,14-,17-/m1/s1

Standard InChI Key:  YKCFRYNFIUFWOG-LSCFUAHRSA-N

Alternative Forms

1. Parent:

   

   ALA259868

   (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-phenylmethoxypurin-9-yl)oxolane-3,4-diol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 358.35

Molecular Weight (Monoisotopic): 358.1277

AlogP: 0.02

#Rotatable Bonds: 5

Polar Surface Area: 122.75

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.45

CX Basic pKa: 2.48

CX LogP: 0.30

CX LogD: 0.30

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.58

Np Likeness Score: 0.56

References

1. Zhu Z, Buolamwini JK..  (2008)  Constrained NBMPR analogue synthesis, pharmacophore mapping and 3D-QSAR modeling of equilibrative nucleoside transporter 1 (ENT1) inhibitory activity.,  16  (7): [PMID:18289860] [10.1016/j.bmc.2008.01.044]

2. Drenichev MS, Oslovsky VE, Sun L, Tijsma A, Kurochkin NN, Tararov VI, Chizhov AO, Neyts J, Pannecouque C, Leyssen P, Mikhailov SN..  (2016)  Modification of the length and structure of the linker of N(6)-benzyladenosine modulates its selective antiviral activity against enterovirus 71.,  111  [PMID:26854380] [10.1016/j.ejmech.2016.01.036]

3. Bonnac LF, Dreis CD, Geraghty RJ..  (2020)  Structure activity relationship, 6-modified purine riboside analogues to activate hSTING, stimulator of interferon genes.,  30  (2): [PMID:31780305] [10.1016/j.bmcl.2019.126819]

Source

Source(1):

• Scientific Literature