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

ID: ALA607777

Chembl Id: CHEMBL607777

PubChem CID: 46876290

Max Phase: Preclinical

Molecular Formula: C16H16FN5O4

Molecular Weight: 361.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1OC(n2cnc3c(Nc4cccc(F)c4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H16FN5O4/c17-8-2-1-3-9(4-8)21-14-11-15(19-6-18-14)22(7-20-11)16-13(25)12(24)10(5-23)26-16/h1-4,6-7,10,12-13,16,23-25H,5H2,(H,18,19,21)/t10-,12-,13-,16?/m1/s1

Standard InChI Key:  CGBXXQWVMLPKMU-AARXTDBFSA-N

Alternative Forms

1. Parent:

   

   ALA607777

   (3R,4S,5R)-2-[6-(3-fluoroanilino)purin-9-yl]-5-(hydroxymethyl)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: 361.33

Molecular Weight (Monoisotopic): 361.1186

AlogP: 0.32

#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: 12.43

CX Basic pKa: 2.28

CX LogP: 0.32

CX LogD: 0.32

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.52

Np Likeness Score: 0.02

References

1. 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]

2. 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]

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]

Source

Source(1):

• Scientific Literature