ID: ALA27047

Max Phase: Preclinical

Molecular Formula: C13H12N4O3

Molecular Weight: 272.26

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  Cn1c(=O)c2nc(-c3ccc(O)cc3)[nH]c2n(C)c1=O

Standard InChI:  InChI=1S/C13H12N4O3/c1-16-11-9(12(19)17(2)13(16)20)14-10(15-11)7-3-5-8(18)6-4-7/h3-6,18H,1-2H3,(H,14,15)

Standard InChI Key:  YGBHMJNRSBKDLF-UHFFFAOYSA-N

Associated Targets(Human)

Adenosine A2b receptor 7672 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Adenosine A2 receptor 1064 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Adenosine A1 receptor 1027 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Bos taurus 956 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Adenosine A1 receptor 6163 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Adenosine A2a receptor 89 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

Properties

Molecular Weight: 272.26Molecular Weight (Monoisotopic): 272.0909AlogP: 0.33#Rotatable Bonds: 1
Polar Surface Area: 92.91Molecular Species: NEUTRALHBA: 6HBD: 2
#RO5 Violations: 0HBA (Lipinski): 7HBD (Lipinski): 2#RO5 Violations (Lipinski): 0
CX Acidic pKa: 7.78CX Basic pKa: 1.81CX LogP: 0.91CX LogD: 0.78
Aromatic Rings: 3Heavy Atoms: 20QED Weighted: 0.67Np Likeness Score: -0.45

References

1. Hamilton HW, Ortwine DF, Worth DF, Badger EW, Bristol JA, Bruns RF, Haleen SJ, Steffen RP..  (1985)  Synthesis of xanthines as adenosine antagonists, a practical quantitative structure-activity relationship application.,  28  (8): [PMID:2991519] [10.1021/jm00146a016]
2. Jacobson KA, Kirk KL, Padgett WL, Daly JW..  (1985)  Functionalized congeners of 1,3-dialkylxanthines: preparation of analogues with high affinity for adenosine receptors.,  28  (9): [PMID:2993622] [10.1021/jm00147a038]
3. 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]
4. 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]

Source