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ID: ALA584554
Max Phase: Preclinical
Molecular Formula: C26H28N4O2
Molecular Weight: 428.54
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCN(CC)C(=O)[C@@H]1C=C2c3cccc4[nH]cc(c34)C[C@H]2N(C(=O)Nc2ccccc2)C1
Standard InChI: InChI=1S/C26H28N4O2/c1-3-29(4-2)25(31)18-13-21-20-11-8-12-22-24(20)17(15-27-22)14-23(21)30(16-18)26(32)28-19-9-6-5-7-10-19/h5-13,15,18,23,27H,3-4,14,16H2,1-2H3,(H,28,32)/t18-,23-/m1/s1
Standard InChI Key: QIPWTYSOANVUKJ-WZONZLPQSA-N
Associated Targets(Human)
Beta-1 adrenergic receptor 6630 Activities
Alpha-2c adrenergic receptor 4876 Activities
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Alpha-2a adrenergic receptor 9450 Activities
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Dopamine D4 receptor 7907 Activities
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Dopamine D3 receptor 14368 Activities
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Dopamine D2 receptor 23596 Activities
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Dopamine D1 receptor 9720 Activities
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Serotonin 7 (5-HT7) receptor 5576 Activities
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Serotonin 6 (5-HT6) receptor 9749 Activities
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Serotonin 2c (5-HT2c) receptor 11471 Activities
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Serotonin 2b (5-HT2b) receptor 10323 Activities
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Serotonin 2a (5-HT2a) receptor 14758 Activities
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Serotonin 1a (5-HT1a) receptor 14969 Activities
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Homo sapiens 32628 Activities
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HERG 29587 Activities
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Cytochrome P450 3A4 53859 Activities
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Cytochrome P450 2D6 33882 Activities
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Cytochrome P450 2C19 29246 Activities
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Cytochrome P450 1A2 26471 Activities
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Cytochrome P450 2C9 32119 Activities
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C-X-C chemokine receptor type 3 2736 Activities
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Associated Targets(non-human)
Rattus norvegicus 775804 Activities
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C-X-C chemokine receptor type 3 96 Activities
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C-X-C chemokine receptor type 3 21 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: 428.54 | Molecular Weight (Monoisotopic): 428.2212 | AlogP: 4.51 | #Rotatable Bonds: 4 |
| Polar Surface Area: 68.44 | Molecular Species: NEUTRAL | HBA: 2 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 6 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 13.36 | CX Basic pKa: | CX LogP: 3.42 | CX LogD: 3.42 |
| Aromatic Rings: 3 | Heavy Atoms: 32 | QED Weighted: 0.64 | Np Likeness Score: -0.19 |
References
| 1. Thoma G, Baenteli R, Lewis I, Wagner T, Oberer L, Blum W, Glickman F, Streiff MB, Zerwes HG.. (2009) Special ergolines are highly selective, potent antagonists of the chemokine receptor CXCR3: discovery, characterization and preliminary SAR of a promising lead., 19 (21): [PMID:19783143] [10.1016/j.bmcl.2009.09.002] |
| 2. Thoma G, Baenteli R, Lewis I, Jones D, Kovarik J, Streiff MB, Zerwes HG.. (2011) Special ergolines efficiently inhibit the chemokine receptor CXCR3 in blood., 21 (16): [PMID:21764306] [10.1016/j.bmcl.2011.06.070] |
Source
Source(1):