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

ID: ALA1093910

Chembl Id: CHEMBL1093910

PubChem CID: 46886345

Max Phase: Preclinical

Molecular Formula: C17H19N5O5

Molecular Weight: 373.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Nc2ncnc3c2ncn3[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C17H19N5O5/c1-26-10-4-2-9(3-5-10)21-15-12-16(19-7-18-15)22(8-20-12)17-14(25)13(24)11(6-23)27-17/h2-5,7-8,11,13-14,17,23-25H,6H2,1H3,(H,18,19,21)/t11-,13-,14-,17-/m1/s1

Standard InChI Key:  DHSVZMSVSTXYCS-LSCFUAHRSA-N

Alternative Forms

1. Parent:

   

   ALA1093910

   (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(4-methoxyphenylamino)-9H-purin-9-yl)tetrahydrofuran-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: 373.37

Molecular Weight (Monoisotopic): 373.1386

AlogP: 0.19

#Rotatable Bonds: 5

Polar Surface Area: 134.78

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: 3.51

CX LogP: 0.02

CX LogD: 0.02

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: 0.40

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. 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]

3. 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]

4. 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]

5. 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]

6. Narlawar R, Lane JR, Doddareddy M, Lin J, Brussee J, Ijzerman AP..  (2010)  Hybrid ortho/allosteric ligands for the adenosine A(1) receptor.,  53  (8): [PMID:20345101] [10.1021/jm901252a]

Source

Source(1):

• Scientific Literature