8-Phenyl-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

ID: ALA158507

Chembl Id: CHEMBL158507

Cas Number: 85872-53-3

PubChem CID: 128784

Product Number: D134588

Max Phase: Preclinical

Molecular Formula: C17H20N4O2

Molecular Weight: 312.37

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)c2nc(-c3ccccc3)[nH]c2n(CCC)c1=O

Standard InChI:  InChI=1S/C17H20N4O2/c1-3-10-20-15-13(16(22)21(11-4-2)17(20)23)18-14(19-15)12-8-6-5-7-9-12/h5-9H,3-4,10-11H2,1-2H3,(H,18,19)

Standard InChI Key:  CLIGSMOZKDCDRZ-UHFFFAOYSA-N

Alternative Forms

Associated Targets(Human)

ADORA2B Tclin Adenosine A2b receptor (7672 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA2B Tclin Adenosine A2 receptor (1064 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA2A Tclin Adenosine A2a receptor (16305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Adora1 Adenosine A1 receptor (6163 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adora2a Adenosine A2a receptor (3360 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adora2b Adenosine A2 receptor (1828 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adora2b Adenosine receptors; A1 & A2 (886 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA2A Adenosine A2a receptor (89 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA1 Adenosine A1 receptor (1027 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bos taurus (956 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rorc Nuclear receptor ROR-gamma (89407 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 312.37Molecular Weight (Monoisotopic): 312.1586AlogP: 2.37#Rotatable Bonds: 5
Polar Surface Area: 72.68Molecular Species: NEUTRALHBA: 5HBD: 1
#RO5 Violations: 0HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski): 0
CX Acidic pKa: 7.69CX Basic pKa: 1.73CX LogP: 2.97CX LogD: 2.82
Aromatic Rings: 3Heavy Atoms: 23QED Weighted: 0.79Np Likeness Score: -0.97

References

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3. Dooley MJ, Quinn RJ.  (1992)  An explanation of the substituent effect of 1,3,8-trisubstituted xanthines on adenosine A1/A2 affinity.,  (10): [10.1016/S0960-894X(00)80213-9]
4. Shamim MT, Ukena D, Padgett WL, Daly JW..  (1989)  Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions.,  32  (6): [PMID:2724296] [10.1021/jm00126a014]
5. Erickson RH, Hiner RN, Feeney SW, Blake PR, Rzeszotarski WJ, Hicks RP, Costello DG, Abreu ME..  (1991)  1,3,8-trisubstituted xanthines. Effects of substitution pattern upon adenosine receptor A1/A2 affinity.,  34  (4): [PMID:2016719] [10.1021/jm00108a029]
6. Daly JW, Padgett WL, Shamim MT..  (1986)  Analogues of 1,3-dipropyl-8-phenylxanthine: enhancement of selectivity at A1-adenosine receptors by aryl substituents.,  29  (8): [PMID:3016270] [10.1021/jm00158a034]
7. Grahner B, Winiwarter S, Lanzner W, Müller CE..  (1994)  Synthesis and structure-activity relationships of deazaxanthines: analogs of potent A1- and A2-adenosine receptor antagonists.,  37  (10): [PMID:8182711] [10.1021/jm00036a019]
8. Jacobson KA, Kiriasis L, Barone S, Bradbury BJ, Kammula U, Campagne JM, Secunda S, Daly JW, Neumeyer JL, Pfleiderer W..  (1989)  Sulfur-containing 1,3-dialkylxanthine derivatives as selective antagonists at A1-adenosine receptors.,  32  (8): [PMID:2754711] [10.1021/jm00128a031]
9. Kim SA, Marshall MA, Melman N, Kim HS, Müller CE, Linden J, Jacobson KA..  (2002)  Structure-activity relationships at human and rat A2B adenosine receptors of xanthine derivatives substituted at the 1-, 3-, 7-, and 8-positions.,  45  (11): [PMID:12014951] [10.1021/jm0104318]
10. Jacobson KA, Ukena D, Padgett W, Daly JW, Kirk KL..  (1987)  Xanthine functionalized congeners as potent ligands at A2-adenosine receptors.,  30  (1): [PMID:3806597] [10.1021/jm00384a037]
11. Jacobson KA, Shi D, Gallo-Rodriguez C, Manning M, Müller C, Daly JW, Neumeyer JL, Kiriasis L, Pfleiderer W..  (1993)  Effect of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors.,  36  (18): [PMID:8410976] [10.1021/jm00070a007]
12. Daly JW, Padgett W, Shamim MT, Butts-Lamb P, Waters J..  (1985)  1,3-Dialkyl-8-(p-sulfophenyl)xanthines: potent water-soluble antagonists for A1- and A2-adenosine receptors.,  28  (4): [PMID:2984420] [10.1021/jm00382a018]
13. Shamim MT, Ukena D, Padgett WL, Hong O, Daly JW..  (1988)  8-Aryl-and 8-cycloalkyl-1,3-dipropylxanthines: further potent and selective antagonists for A1-adenosine receptors.,  31  (3): [PMID:3346878] [10.1021/jm00398a020]
14. 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]
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