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ID: ALA464099
Max Phase: Preclinical
Molecular Formula: C20H23NO4
Molecular Weight: 341.41
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): N-Methyllaurotetanine
Synonyms from Alternative Forms(1):
Canonical SMILES: COc1cc2c(cc1O)C[C@H]1c3c(cc(OC)c(OC)c3-2)CCN1C
Standard InChI: InChI=1S/C20H23NO4/c1-21-6-5-11-9-17(24-3)20(25-4)19-13-10-16(23-2)15(22)8-12(13)7-14(21)18(11)19/h8-10,14,22H,5-7H2,1-4H3/t14-/m0/s1
Standard InChI Key: ZFLRVRLYWHNAEC-AWEZNQCLSA-N
Associated Targets(Human)
Serotonin 1a (5-HT1a) receptor 14969 Activities
Alpha-1d adrenergic receptor 4171 Activities
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Alpha-1a adrenergic receptor 8359 Activities
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Serotonin 3a (5-HT3a) receptor 3366 Activities
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Serotonin 2a (5-HT2a) receptor 14758 Activities
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Serotonin 1e (5-HT1e) receptor 696 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 5a (5-HT5a) receptor 1433 Activities
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Serotonin 2b (5-HT2b) receptor 10323 Activities
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Alpha-2b adrenergic receptor 4412 Activities
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Dopamine D2 receptor 23596 Activities
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Dopamine D4 receptor 7907 Activities
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Dopamine D5 receptor 1597 Activities
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Delta opioid receptor 15096 Activities
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Histamine H1 receptor 7573 Activities
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Histamine H3 receptor 10389 Activities
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Histamine H4 receptor 3997 Activities
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Kappa opioid receptor 16155 Activities
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Muscarinic acetylcholine receptor M1 12690 Activities
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Muscarinic acetylcholine receptor M2 10671 Activities
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Muscarinic acetylcholine receptor M3 7750 Activities
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Muscarinic acetylcholine receptor M4 6041 Activities
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Muscarinic acetylcholine receptor M5 4677 Activities
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Mu opioid receptor 19785 Activities
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Serotonin 2c (5-HT2c) receptor 11471 Activities
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Alpha-1b adrenergic receptor 2912 Activities
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Alpha-2c adrenergic receptor 4876 Activities
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Beta-2 adrenergic receptor 11824 Activities
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Dopamine D3 receptor 14368 Activities
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Dopamine transporter 10535 Activities
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Norepinephrine transporter 10102 Activities
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Serotonin transporter 12625 Activities
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Neutrophil 395 Activities
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Associated Targets(non-human)
Plasmodium falciparum 966862 Activities
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Vero 26788 Activities
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Poliovirus 2 222 Activities
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Peripheral-type benzodiazepine receptor 1942 Activities
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Sigma-1 receptor 3326 Activities
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Acetylcholinesterase 12221 Activities
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Cholinesterase 8742 Activities
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Molecule Features
| Natural Product: Yes | 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: 341.41 | Molecular Weight (Monoisotopic): 341.1627 | AlogP: 3.17 | #Rotatable Bonds: 3 |
| Polar Surface Area: 51.16 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 9.71 | CX Basic pKa: 7.02 | CX LogP: 2.92 | CX LogD: 2.77 |
| Aromatic Rings: 2 | Heavy Atoms: 25 | QED Weighted: 0.93 | Np Likeness Score: 1.55 |
References
| 1. Boustie J, Stigliani JL, Montanha J, Amoros M, Payard M, Girre L.. (1998) Antipoliovirus structure-activity relationships of some aporphine alkaloids., 61 (4): [PMID:9584402] [10.1021/np970382v] |
| 2. Gafner S, Dietz BM, McPhail KL, Scott IM, Glinski JA, Russell FE, McCollom MM, Budzinski JW, Foster BC, Bergeron C, Rhyu MR, Bolton JL.. (2006) Alkaloids from Eschscholzia californica and their capacity to inhibit binding of [3H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT1A receptors in Vitro., 69 (3): [PMID:16562853] [10.1021/np058114h] |
| 3. Böhlke M, Guinaudeau H, Angerhofer CK, Wongpanich V, Soejarto DD, Farnsworth NR, Mora GA, Poveda LJ.. (1996) Costaricine, a new antiplasmodial bisbenzylisoquinoline alkaloid from Nectandra salicifolia trunk bark., 59 (6): [PMID:8786363] [10.1021/np960195h] |
| 4. Madapa S, Harding WW.. (2015) Semisynthetic Studies on and Biological Evaluation of N-Methyllaurotetanine Analogues as Ligands for 5-HT Receptors., 78 (4): [PMID:25695425] [10.1021/np500893h] |
| 5. Wan Othman WN, Liew SY, Khaw KY, Murugaiyah V, Litaudon M, Awang K.. (2016) Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae)., 24 (18): [PMID:27492195] [10.1016/j.bmc.2016.07.043] |
| 6. Kuo PC,Wu YH,Hung HY,Lam SH,Ma GH,Kuo LM,Hwang TL,Kuo DH,Wu TS. (2020) Anti-inflammatory principles from Lindera aggregata., 30 (13): [PMID:32359855] [10.1016/j.bmcl.2020.127224] |
Source
Source(1):