8-(3-Oxa-tricyclo[3.2.1.0*2,4*]oct-6-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

ID: ALA298474

Chembl Id: CHEMBL298474

Cas Number: 166181-76-6

PubChem CID: 9798222

Max Phase: Preclinical

Molecular Formula: C18H24N4O3

Molecular Weight: 344.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)c2nc(C3CC4CC3C3OC43)[nH]c2n(CCC)c1=O

Standard InChI:  InChI=1S/C18H24N4O3/c1-3-5-21-16-12(17(23)22(6-4-2)18(21)24)19-15(20-16)11-8-9-7-10(11)14-13(9)25-14/h9-11,13-14H,3-8H2,1-2H3,(H,19,20)

Standard InChI Key:  OQCJPFYWFGUHIN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA298474

   8-(1S,2R,4S,5S,6R)-3-Oxatricyclo(3.2.1.02,4)oct-6-yl-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione

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: 344.42

Molecular Weight (Monoisotopic): 344.1848

AlogP: 1.60

#Rotatable Bonds: 5

Polar Surface Area: 85.21

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.53

CX Basic pKa: 2.57

CX LogP: 1.71

CX LogD: 1.68

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.02

References

1. Pfister JR, Belardinelli L, Lee G, Lum RT, Milner P, Stanley WC, Linden J, Baker SP, Schreiner G..  (1997)  Synthesis and biological evaluation of the enantiomers of the potent and selective A1-adenosine antagonist 1,3-dipropyl-8-[2-(5,6-epoxynorbonyl)]-xanthine.,  40  (12): [PMID:9191953] [10.1021/jm970013w]

2. Pfister JR, Belardinelli L, Lee G, Lum RT, Milner P, Stanley WC, Linden J, Baker SP, Schreiner G..  (1997)  Synthesis and biological evaluation of the enantiomers of the potent and selective A1-adenosine antagonist 1,3-dipropyl-8-[2-(5,6-epoxynorbonyl)]-xanthine.,  40  (12): [PMID:9191953] [10.1021/jm970013w]

3. Pfister JR, Belardinelli L, Lee G, Lum RT, Milner P, Stanley WC, Linden J, Baker SP, Schreiner G..  (1997)  Synthesis and biological evaluation of the enantiomers of the potent and selective A1-adenosine antagonist 1,3-dipropyl-8-[2-(5,6-epoxynorbonyl)]-xanthine.,  40  (12): [PMID:9191953] [10.1021/jm970013w]

4. Faudone G, Arifi S, Merk D..  (2021)  The Medicinal Chemistry of Caffeine.,  64  (11.0): [PMID:34019396] [10.1021/acs.jmedchem.1c00261]

Source

Source(1):

• Scientific Literature