2-Hydroxymethyl-5-[6-(4-phenyl-butylamino)-purin-9-yl]-tetrahydro-furan-3,4-diol

ID: ALA2113406

Chembl Id: CHEMBL2113406

Cas Number: 101565-58-6

PubChem CID: 71355811

Max Phase: Preclinical

Molecular Formula: C20H25N5O4

Molecular Weight: 399.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c(NCCCCc4ccccc4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C20H25N5O4/c26-10-14-16(27)17(28)20(29-14)25-12-24-15-18(22-11-23-19(15)25)21-9-5-4-8-13-6-2-1-3-7-13/h1-3,6-7,11-12,14,16-17,20,26-28H,4-5,8-10H2,(H,21,22,23)/t14-,16-,17-,20-/m1/s1

Standard InChI Key:  QNQVVNSRYWTXJV-WVSUBDOOSA-N

Alternative Forms

1. Parent:

   

   ALA2113406

   N-(4-Phenylbutyl)adenosine

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: 399.45

Molecular Weight (Monoisotopic): 399.1907

AlogP: 0.87

#Rotatable Bonds: 8

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: 3.76

CX LogP: 1.11

CX LogD: 1.11

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: 0.51

References

1. 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]

2. 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]

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. 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]

5. Bednarska-Szczepaniak K, Mieczkowski A, Kierozalska A, Pavlović Saftić D, Głąbała K, Przygodzki T, Stańczyk L, Karolczak K, Watała C, Rao H, Gao ZG, Jacobson KA, Leśnikowski ZJ..  (2021)  Synthesis and evaluation of adenosine derivatives as A₁, A_2A, A_2B and A₃ adenosine receptor ligands containing boron clusters as phenyl isosteres and selective A₃ agonists.,  223  [PMID:34171656] [10.1016/j.ejmech.2021.113607]

Source

Source(1):

• Scientific Literature