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ID: ALA5170576
Max Phase: Preclinical
Molecular Formula: C20H28N4O3
Molecular Weight: 372.47
Associated Items:
Representations
Canonical SMILES: COC(=O)Nc1cc(-c2ccc(OC[C@@](C)(N)CC(C)C)c(C)n2)ccn1
Standard InChI: InChI=1S/C20H28N4O3/c1-13(2)11-20(4,21)12-27-17-7-6-16(23-14(17)3)15-8-9-22-18(10-15)24-19(25)26-5/h6-10,13H,11-12,21H2,1-5H3,(H,22,24,25)/t20-/m0/s1
Standard InChI Key: HINOQCZIDBNXEI-FQEVSTJZSA-N
Associated Targets(Human)
Adaptor-associated kinase 1053 Activities
Cytochrome P450 3A4 53859 Activities
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Cytochrome P450 1A2 26471 Activities
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Cytochrome P450 2C19 29246 Activities
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Cytochrome P450 2C9 32119 Activities
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Cytochrome P450 2D6 33882 Activities
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Cytochrome P450 2B6 1338 Activities
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HERG 29587 Activities
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Serotonin 2b (5-HT2b) receptor 10323 Activities
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BMP-2-inducible protein kinase 723 Activities
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Death-associated protein kinase 1 1664 Activities
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Serine/threonine-protein kinase GAK 1150 Activities
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MAP kinase-interacting serine/threonine-protein kinase MNK1 2071 Activities
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MAP kinase signal-integrating kinase 2 3518 Activities
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myosin light chain kinase 2 424 Activities
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Associated Targets(non-human)
AP2-associated protein kinase 1 50 Activities
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Rattus norvegicus 775804 Activities
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Molecule Features
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: | 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: 372.47 | Molecular Weight (Monoisotopic): 372.2161 | AlogP: 3.77 | #Rotatable Bonds: 7 |
| Polar Surface Area: 99.36 | Molecular Species: BASE | HBA: 6 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 12.88 | CX Basic pKa: 9.80 | CX LogP: 3.15 | CX LogD: 0.84 |
| Aromatic Rings: 2 | Heavy Atoms: 27 | QED Weighted: 0.77 | Np Likeness Score: -0.79 |
References
| 1. Luo G, Chen L, Kostich WA, Hamman B, Allen J, Easton A, Bourin C, Gulianello M, Lippy J, Nara S, Pattipati SN, Dandapani K, Dokania M, Vattikundala P, Sharma V, Elavazhagan S, Verma MK, Lal Das M, Wagh S, Balakrishnan A, Johnson BM, Santone KS, Thalody G, Denton R, Saminathan H, Holenarsipur VK, Kumar A, Rao A, Putlur SP, Sarvasiddhi SK, Shankar G, Louis JV, Ramarao M, Conway CM, Li YW, Pieschl R, Tian Y, Hong Y, Bristow L, Albright CF, Bronson JJ, Macor JE, Dzierba CD.. (2022) Discovery and Optimization of Biaryl Alkyl Ethers as a Novel Class of Highly Selective, CNS-Penetrable, and Orally Active Adaptor Protein-2-Associated Kinase 1 (AAK1) Inhibitors for the Potential Treatment of Neuropathic Pain., 65 (6.0): [PMID:35261239] [10.1021/acs.jmedchem.1c02132] |
Source
Source(1):