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ID: ALA252048
Max Phase: Preclinical
Molecular Formula: C20H17ClN8O3
Molecular Weight: 452.86
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): CVT-6694
Synonyms from Alternative Forms(1):
Canonical SMILES: CCCn1c(=O)[nH]c2nc(-c3cnn(Cc4noc(-c5ccc(Cl)cc5)n4)c3)[nH]c2c1=O
Standard InChI: InChI=1S/C20H17ClN8O3/c1-2-7-29-19(30)15-17(26-20(29)31)25-16(24-15)12-8-22-28(9-12)10-14-23-18(32-27-14)11-3-5-13(21)6-4-11/h3-6,8-9H,2,7,10H2,1H3,(H,24,25)(H,26,31)
Standard InChI Key: HWHLLTUJISZFDN-UHFFFAOYSA-N
Associated Targets(Human)
ADORA2B Tclin Adenosine A2b receptor (7672 Activities)
ADORA1 Tclin Adenosine A1 receptor (17603 Activities)
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ADORA2A Tclin Adenosine A2a receptor (16305 Activities)
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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
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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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 452.86 | Molecular Weight (Monoisotopic): 452.1112 | AlogP: 2.44 | #Rotatable Bonds: 6 |
| Polar Surface Area: 140.28 | Molecular Species: NEUTRAL | HBA: 9 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 11 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: 6.76 | CX Basic pKa: 1.19 | CX LogP: 3.90 | CX LogD: 3.38 |
| Aromatic Rings: 5 | Heavy Atoms: 32 | QED Weighted: 0.40 | Np Likeness Score: -1.88 |
References
| 1. Kalla RV, Elzein E, Perry T, Li X, Gimbel A, Yang M, Zeng D, Zablocki J.. (2008) Selective, high affinity A(2B) adenosine receptor antagonists: N-1 monosubstituted 8-(pyrazol-4-yl)xanthines., 18 (4): [PMID:18226896] [10.1016/j.bmcl.2008.01.008] |
| 2. Cheng F, Cheng F, Xu Z, Liu G, Tang Y.. (2010) Insights into binding modes of adenosine A(2B) antagonists with ligand-based and receptor-based methods., 45 (8): [PMID:20537438] [10.1016/j.ejmech.2010.04.039] |
| 3. El Maatougui A, Azuaje J, González-Gómez M, Miguez G, Crespo A, Carbajales C, Escalante L, García-Mera X, Gutiérrez-de-Terán H, Sotelo E.. (2016) Discovery of Potent and Highly Selective A2B Adenosine Receptor Antagonist Chemotypes., 59 (5): [PMID:26824742] [10.1021/acs.jmedchem.5b01586] |
| 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):