ID: ALA411066

Max Phase: Preclinical

Molecular Formula: C15H17N5O5

Molecular Weight: 347.33

Molecule Type: Small molecule

Representations

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c(NCc4ccco4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H17N5O5/c21-5-9-11(22)12(23)15(25-9)20-7-19-10-13(17-6-18-14(10)20)16-4-8-2-1-3-24-8/h1-3,6-7,9,11-12,15,21-23H,4-5H2,(H,16,17,18)/t9-,11-,12-,15-/m1/s1

Standard InChI Key:  CAGLGYNQQSIUGX-SDBHATRESA-N

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 347.33

Molecular Weight (Monoisotopic): 347.1230

AlogP: -0.36

#Rotatable Bonds: 5

Polar Surface Area: 138.69

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.45

CX Basic pKa: 4.67

CX LogP: -1.00

CX LogD: -1.00

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.49

Np Likeness Score: 0.24

References

1. Siddiqi SM, Jacobson KA, Esker JL, Olah ME, Ji XD, Melman N, Tiwari KN, Secrist JA, Schneller SW, Cristalli G..  (1995)  Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.,  38  (7): [PMID:7707320] [10.1021/jm00007a014]

2. Bressi JC, Choe J, Hough MT, Buckner FS, Van Voorhis WC, Verlinde CL, Hol WG, Gelb MH..  (2000)  Adenosine analogues as inhibitors of Trypanosoma brucei phosphoglycerate kinase: elucidation of a novel binding mode for a 2-amino-N(6)-substituted adenosine.,  43  (22): [PMID:11063610] [10.1021/jm000287a]

3. Kusachi S, Thompson RD, Yamada N, Daly DT, Olsson RA..  (1986)  Dog coronary artery adenosine receptor: structure of the N6-aryl subregion.,  29  (6): [PMID:3012086] [10.1021/jm00156a016]

4. 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]

5. Cappellacci L, Franchetti P, Vita P, Petrelli R, Lavecchia A, Jayaram HN, Saiko P, Graser G, Szekeres T, Grifantini M..  (2008)  Ribose-modified purine nucleosides as ribonucleotide reductase inhibitors. Synthesis, antitumor activity, and molecular modeling of N6-substituted 3'-C-methyladenosine derivatives.,  51  (14): [PMID:18588281] [10.1021/jm800205c]

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

12. Vistoli G, Brizzolari A, Faioni E, Razzari C, Santaniello E..  (2014)  Naturally occurring N(6)-substituted adenosines (cytokinin ribosides) are in vitro inhibitors of platelet aggregation: an in silico evaluation of their interaction with the P2Y(12) receptor.,  24  (24): [PMID:25467153] [10.1016/j.bmcl.2014.10.080]

13. 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]

14. Orlov AA, Drenichev MS, Oslovsky VE, Kurochkin NN, Solyev PN, Kozlovskaya LI, Palyulin VA, Karganova GG, Mikhailov SN, Osolodkin DI..  (2017)  New tools in nucleoside toolbox of tick-borne encephalitis virus reproduction inhibitors.,  27  (5): [PMID:28159412] [10.1016/j.bmcl.2017.01.040]

15. Osgerby L, Lai YC, Thornton PJ, Amalfitano J, Le Duff CS, Jabeen I, Kadri H, Miccoli A, Tucker JHR, Muqit MMK, Mehellou Y..  (2017)  Kinetin Riboside and Its ProTides Activate the Parkinson's Disease Associated PTEN-Induced Putative Kinase 1 (PINK1) Independent of Mitochondrial Depolarization.,  60  (8): [PMID:28323427] [10.1021/acs.jmedchem.6b01897]

16. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• IMI-CARE SARS-CoV-2 Data