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ID: ALA1086473
Max Phase: Preclinical
Molecular Formula: C21H22N4
Molecular Weight: 330.44
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCCCc1nc2c(N)nc3ccccc3c2n1Cc1ccccc1
Standard InChI: InChI=1S/C21H22N4/c1-2-3-13-18-24-19-20(25(18)14-15-9-5-4-6-10-15)16-11-7-8-12-17(16)23-21(19)22/h4-12H,2-3,13-14H2,1H3,(H2,22,23)
Standard InChI Key: CQBDMXYZNLJUFT-UHFFFAOYSA-N
Associated Targets(Human)
Toll-like receptor 8 1853 Activities
Blood 2950 Activities
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Toll-like receptor 7 2626 Activities
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Associated Targets(non-human)
Plasmodium berghei 192651 Activities
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TLR7 and TLR8 70 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: 330.44 | Molecular Weight (Monoisotopic): 330.1844 | AlogP: 4.56 | #Rotatable Bonds: 5 |
| Polar Surface Area: 56.73 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 4.87 | CX LogP: 4.84 | CX LogD: 4.84 |
| Aromatic Rings: 4 | Heavy Atoms: 25 | QED Weighted: 0.58 | Np Likeness Score: -0.92 |
References
| 1. Shukla NM, Malladi SS, Mutz CA, Balakrishna R, David SA.. (2010) Structure-activity relationships in human toll-like receptor 7-active imidazoquinoline analogues., 53 (11): [PMID:20481492] [10.1021/jm100358c] |
| 2. Kokatla HP, Sil D, Malladi SS, Balakrishna R, Hermanson AR, Fox LM, Wang X, Dixit A, David SA.. (2013) Exquisite selectivity for human toll-like receptor 8 in substituted furo[2,3-c]quinolines., 56 (17): [PMID:23899291] [10.1021/jm400694d] |
| 3. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds, [10.6019/CHEMBL3301361] |
| 4. Saroa R, Kaushik D, Bagai U, Kaur S, Salunke DB.. (2019) Efficacy of TLR7 agonistic imidazoquinoline as immunochemotherapeutic agent against P. Berghei ANKA infected rodent host., 29 (9): [PMID:30850167] [10.1016/j.bmcl.2019.02.029] |
| 5. Kimani FW, Manna S, Moser B, Shen J, Nihesh N, Esser-Kahn AP.. (2021) Improving the Adjuvanticity of Small Molecule Immune Potentiators Using Covalently Linked NF-κB Modulators., 12 (9.0): [PMID:34527180] [10.1021/acsmedchemlett.1c00267] |
Source
Source(2):