2-Hydroxymethyl-5-(6-phenylamino-purin-9-yl)-tetrahydro-furan-3,4-diol

ID: ALA262083

Chembl Id: CHEMBL262083

Cas Number: 23589-16-4

PubChem CID: 101430

Max Phase: Preclinical

Molecular Formula: C16H17N5O4

Molecular Weight: 343.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: N6-Phenyladenosine | N6-Phenyladenosine|23589-16-4|Adenosine, N-phenyl-|N(6)-Phenyladenosine|(2R,3R,4S,5R)-2-(6-anilinopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol|MLS000069355|SMR000058677|(2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(6-(phenylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol|(2R,3R,4S,5R)-2-(6-anilino-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol|NSC 517192|Opera_ID_298|MLS001074192|MLS002153269|CHEMBL262083|cid_101430|SCHEMBL1050156|REGID_for_CID_101430|BDBM42467|CHEBI:112766|DTXSID80101720Show More⌵

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

Standard InChI:  InChI=1S/C16H17N5O4/c22-6-10-12(23)13(24)16(25-10)21-8-19-11-14(17-7-18-15(11)21)20-9-4-2-1-3-5-9/h1-5,7-8,10,12-13,16,22-24H,6H2,(H,17,18,20)/t10-,12-,13-,16-/m1/s1

Standard InChI Key:  QVUUUSJUORLECR-XNIJJKJLSA-N

Alternative Forms

1. Parent:

   

   ALA262083

   N6-PHENYLADENOSINE

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

Calculated Properties

Molecular Weight: 343.34

Molecular Weight (Monoisotopic): 343.1281

AlogP: 0.18

#Rotatable Bonds: 4

Polar Surface Area: 125.55

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.45

CX Basic pKa: 2.45

CX LogP: 0.18

CX LogD: 0.18

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: 0.44

References

1. Jacobson KA, Kirk KL, Padgett WL, Daly JW..  (1985)  Functionalized congeners of adenosine: preparation of analogues with high affinity for A1-adenosine receptors.,  28  (9): [PMID:2993623] [10.1021/jm00147a039]

2. Bridges AJ, Moos WH, Szotek DL, Trivedi BK, Bristol JA, Heffner TG, Bruns RF, Downs DA..  (1987)  N6-(2,2-diphenylethyl)adenosine, a novel adenosine receptor agonist with antipsychotic-like activity.,  30  (10): [PMID:2888894] [10.1021/jm00393a003]

3. Daly JW..  (1982)  Adenosine receptors: targets for future drugs.,  25  (3): [PMID:6279840] [10.1021/jm00345a001]

4. Sarges R, Howard HR, Browne RG, Lebel LA, Seymour PA, Koe BK..  (1990)  4-Amino[1,2,4]triazolo[4,3-a]quinoxalines. A novel class of potent adenosine receptor antagonists and potential rapid-onset antidepressants.,  33  (8): [PMID:2374150] [10.1021/jm00170a031]

5. Peet NP, Lentz NL, Meng EC, Dudley MW, Ogden AM, Demeter DA, Weintraub HJ, Bey P..  (1990)  A novel synthesis of xanthines: support for a new binding mode for xanthines with respect to adenosine at adenosine receptors.,  33  (12): [PMID:2258897] [10.1021/jm00174a004]

6. Thompson RD, Secunda S, Daly JW, Olsson RA..  (1991)  Activity of N6-substituted 2-chloroadenosines at A1 and A2 adenosine receptors.,  34  (12): [PMID:1766003] [10.1021/jm00116a007]

7. Jacobson KA, Nikodijevic O, Ji XD, Berkich DA, Eveleth D, Dean RL, Hiramatsu K, Kassell NF, van Galen PJ, Lee KS..  (1992)  Synthesis and biological activity of N6-(p-sulfophenyl)alkyl and N6-sulfoalkyl derivatives of adenosine: water-soluble and peripherally selective adenosine agonists.,  35  (22): [PMID:1433217] [10.1021/jm00100a020]

8. Jacobson KA, van Galen PJ, Williams M..  (1992)  Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential.,  35  (3): [PMID:1738138] [10.1021/jm00081a001]

9. van der Wenden EM, Ijzerman AP, Soudijn W..  (1992)  A steric and electrostatic comparison of three models for the agonist/antagonist binding site on the adenosine A1 receptor.,  35  (4): [PMID:1542091] [10.1021/jm00082a003]

10. Kwatra MM, Leung E, Hosey MM, Green RD..  (1987)  N6-phenyladenosines: pronounced effect of phenyl substituents on affinity for A2 adenosine receptors.,  30  (5): [PMID:3572985] [10.1021/jm00388a039]

11. 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]

12. Ivanov AA, Wang B, Klutz AM, Chen VL, Gao ZG, Jacobson KA..  (2008)  Probing distal regions of the A2B adenosine receptor by quantitative structure-activity relationship modeling of known and novel agonists.,  51  (7): [PMID:18321038] [10.1021/jm701442d]

13. 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]

14. 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]

15. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

16. PubChem BioAssay data set, 

17. PubChem BioAssay data set, 

18. PubChem BioAssay data set, 

19. 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]

20. Goswami M, Wilke KE, Carlson EE..  (2017)  Rational Design of Selective Adenine-Based Scaffolds for Inactivation of Bacterial Histidine Kinases.,  60  (19): [PMID:28933546] [10.1021/acs.jmedchem.7b01066]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays