2-[6-Amino-2-(2-cyclohexyl-ethoxy)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA606093

Chembl Id: CHEMBL606093

PubChem CID: 46874471

Max Phase: Preclinical

Molecular Formula: C18H27N5O5

Molecular Weight: 393.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(OCCC2CCCCC2)nc2c1ncn2C1O[C@@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C18H27N5O5/c19-15-12-16(22-18(21-15)27-7-6-10-4-2-1-3-5-10)23(9-20-12)17-14(26)13(25)11(8-24)28-17/h9-11,13-14,17,24-26H,1-8H2,(H2,19,21,22)/t11-,13-,14-,17?/m0/s1

Standard InChI Key:  VHMUQIWMOXQFBP-JVCSGSNQSA-N

Alternative Forms

1. Parent:

   

   ALA606093

   (3S,4R,5S)-2-[6-amino-2-(2-cyclohexylethoxy)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: 393.44

Molecular Weight (Monoisotopic): 393.2012

AlogP: 0.37

#Rotatable Bonds: 6

Polar Surface Area: 148.77

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 4.22

CX LogP: 0.91

CX LogD: 0.91

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: 0.72

References

1. Ueeda M, Thompson RD, Arroyo LH, Olsson RA..  (1991)  2-Alkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor.,  34  (4): [PMID:2016707] [10.1021/jm00108a014]

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

Source

Source(1):

• Scientific Literature