5-(1,3-Dibutyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methylamide

ID: ALA138746

Chembl Id: CHEMBL138746

PubChem CID: 11743031

Max Phase: Preclinical

Molecular Formula: C19H29N5O6

Molecular Weight: 423.47

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CCCCn1c(=O)c2c(ncn2[C@@H]2O[C@H](C(=O)NC)[C@@H](O)[C@H]2O)n(CCCC)c1=O

Standard InChI:  InChI=1S/C19H29N5O6/c1-4-6-8-22-15-11(17(28)23(19(22)29)9-7-5-2)24(10-21-15)18-13(26)12(25)14(30-18)16(27)20-3/h10,12-14,18,25-26H,4-9H2,1-3H3,(H,20,27)/t12-,13+,14-,18+/m0/s1

Standard InChI Key:  FOUQIXNUUYCGAU-MOROJQBDSA-N

Alternative Forms

  1. Parent:

    ALA138746

    Dbxrm

Associated Targets(Human)

ADORA3 Tchem Adenosine A3 receptor (15931 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
Adora3 Adenosine A3 receptor (846 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adora2a Adenosine A2a receptor (3360 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adora2a Adenosine receptor A2a and A3 (172 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: 423.47Molecular Weight (Monoisotopic): 423.2118AlogP: -0.67#Rotatable Bonds: 8
Polar Surface Area: 140.61Molecular Species: NEUTRALHBA: 10HBD: 3
#RO5 Violations: HBA (Lipinski): 11HBD (Lipinski): 3#RO5 Violations (Lipinski): 1
CX Acidic pKa: 12.39CX Basic pKa: CX LogP: 0.06CX LogD: 0.06
Aromatic Rings: 2Heavy Atoms: 30QED Weighted: 0.51Np Likeness Score: -0.14

References

1. Gao ZG, Kim SK, Biadatti T, Chen W, Lee K, Barak D, Kim SG, Johnson CR, Jacobson KA..  (2002)  Structural determinants of A(3) adenosine receptor activation: nucleoside ligands at the agonist/antagonist boundary.,  45  (20): [PMID:12238926] [10.1021/jm020211+]
2. Baraldi PG, Preti D, Borea PA, Varani K..  (2012)  Medicinal chemistry of A₃ adenosine receptor modulators: pharmacological activities and therapeutic implications.,  55  (12): [PMID:22468757] [10.1021/jm300087j]
3. Faudone G, Arifi S, Merk D..  (2021)  The Medicinal Chemistry of Caffeine.,  64  (11.0): [PMID:34019396] [10.1021/acs.jmedchem.1c00261]

Source