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ID: ALA1170908
Max Phase: Preclinical
Molecular Formula: C24H20ClN3O
Molecular Weight: 401.90
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: O=C(NC[C@@H](c1ccccc1)n1ccnc1)c1ccc(-c2ccc(Cl)cc2)cc1
Standard InChI: InChI=1S/C24H20ClN3O/c25-22-12-10-19(11-13-22)18-6-8-21(9-7-18)24(29)27-16-23(28-15-14-26-17-28)20-4-2-1-3-5-20/h1-15,17,23H,16H2,(H,27,29)/t23-/m0/s1
Standard InChI Key: FHHNSSGZEIVGMS-QHCPKHFHSA-N
Associated Targets(Human)
Cytochrome P450 24A1 161 Activities
25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial 12 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: 401.90 | Molecular Weight (Monoisotopic): 401.1295 | AlogP: 5.22 | #Rotatable Bonds: 6 |
| Polar Surface Area: 46.92 | Molecular Species: NEUTRAL | HBA: 3 | HBD: 1 |
| #RO5 Violations: 1 | HBA (Lipinski): 4 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: | CX Basic pKa: 6.71 | CX LogP: 4.99 | CX LogD: 4.93 |
| Aromatic Rings: 4 | Heavy Atoms: 29 | QED Weighted: 0.48 | Np Likeness Score: -1.31 |
References
| 1. Aboraia AS, Yee SW, Gomaa MS, Shah N, Robotham AC, Makowski B, Prosser D, Brancale A, Jones G, Simons C.. (2010) Synthesis and CYP24A1 inhibitory activity of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides., 18 (14): [PMID:20594862] [10.1016/j.bmc.2010.06.011] |
| 2. Ferla S, Aboraia AS, Brancale A, Pepper CJ, Zhu J, Ochalek JT, DeLuca HF, Simons C.. (2014) Small-molecule inhibitors of 25-hydroxyvitamin D-24-hydroxylase (CYP24A1): synthesis and biological evaluation., 57 (18): [PMID:25148392] [10.1021/jm5009314] |
| 3. Taban IM, Zhu J, DeLuca HF, Simons C.. (2017) Analysis of the binding sites of vitamin D 1α-hydroxylase (CYP27B1) and vitamin D 24-hydroxylase (CYP24A1) for the design of selective CYP24A1 inhibitors: Homology modelling, molecular dynamics simulations and identification of key binding requirements., 25 (20): [PMID:28886997] [10.1016/j.bmc.2017.08.036] |
Source
Source(1):