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ID: ALA5182943
Max Phase: Preclinical
Molecular Formula: C20H22ClFN2O3
Molecular Weight: 356.40
Associated Items:
Representations
Canonical SMILES: COc1cc(OC)c(C2NCCc3c2[nH]c2ccc(F)cc32)cc1OC.Cl
Standard InChI: InChI=1S/C20H21FN2O3.ClH/c1-24-16-10-18(26-3)17(25-2)9-14(16)19-20-12(6-7-22-19)13-8-11(21)4-5-15(13)23-20;/h4-5,8-10,19,22-23H,6-7H2,1-3H3;1H
Standard InChI Key: LWHOEIHANZIFDG-UHFFFAOYSA-N
Associated Targets(Human)
HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)
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HTR2A Tclin Serotonin 2 receptors; 5-HT2a & 5-HT2c (792 Activities)
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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)
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HTR5A Tchem Serotonin 5a (5-HT5a) receptor (1433 Activities)
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HTR6 Tchem Serotonin 6 (5-HT6) receptor (9749 Activities)
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HTR7 Tclin Serotonin 7 (5-HT7) receptor (5576 Activities)
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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)
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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)
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DRD3 Tclin Dopamine D3 receptor (14368 Activities)
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DRD4 Tchem Dopamine D4 receptor (7907 Activities)
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SLC6A4 Tclin Serotonin transporter (12625 Activities)
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SIGMAR1 Tclin Sigma opioid receptor (6358 Activities)
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HTR1E Tchem Serotonin 1e (5-HT1e) receptor (696 Activities)
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HTR1D Tclin Serotonin 1d (5-HT1d) receptor (2897 Activities)
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HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)
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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
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TMEM97 Tchem Sigma intracellular receptor 2 (973 Activities)
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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
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ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)
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ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)
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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)
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ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)
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ADRB3 Tclin Beta-3 adrenergic receptor (5850 Activities)
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DRD1 Tclin Dopamine D1 receptor (9720 Activities)
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DRD2 Tclin Dopamine D2 receptor (23596 Activities)
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DRD5 Tchem Dopamine D5 receptor (1597 Activities)
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HRH1 Tclin Histamine H1 receptor (7573 Activities)
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HRH2 Tclin Histamine H2 receptor (5428 Activities)
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HRH3 Tclin Histamine H3 receptor (10389 Activities)
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HRH4 Tchem Histamine H4 receptor (3997 Activities)
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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)
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CHRM4 Tclin Muscarinic acetylcholine receptor M4 (6041 Activities)
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CHRM5 Tclin Muscarinic acetylcholine receptor M5 (4677 Activities)
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OPRD1 Tclin Delta opioid receptor (15096 Activities)
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OPRK1 Tclin Kappa opioid receptor (16155 Activities)
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OPRM1 Tclin Mu opioid receptor (19785 Activities)
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SLC6A3 Tclin Dopamine transporter (10535 Activities)
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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
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TSPO Tchem Translocator protein (484 Activities)
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GABRA1 Tclin GABA-A receptor; anion channel (986 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: 356.40 | Molecular Weight (Monoisotopic): 356.1536 | AlogP: 3.57 | #Rotatable Bonds: 4 |
| Polar Surface Area: 55.51 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 7.64 | CX LogP: 3.04 | CX LogD: 2.61 |
| Aromatic Rings: 3 | Heavy Atoms: 26 | QED Weighted: 0.75 | Np Likeness Score: 0.02 |
References
| 1. Orr MJ, Cao AB, Wang CT, Gaisin A, Csakai A, Friswold AP, Meltzer HY, McCorvy JD, Scheidt KA.. (2022) Discovery of Highly Potent Serotonin 5-HT2 Receptor Agonists Inspired by Heteroyohimbine Natural Products., 13 (4.0): [PMID:35450369] [10.1021/acsmedchemlett.1c00694] |
Source
Source(1):