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ID: ALA12327
Max Phase: Preclinical
Molecular Formula: C14H16N2O2
Molecular Weight: 244.29
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COC(=O)C1Cc2c([nH]c3ccccc23)C(C)N1
Standard InChI: InChI=1S/C14H16N2O2/c1-8-13-10(7-12(15-8)14(17)18-2)9-5-3-4-6-11(9)16-13/h3-6,8,12,15-16H,7H2,1-2H3
Standard InChI Key: WZHYQHKXXRMALW-UHFFFAOYSA-N
Associated Targets(Human)
Endoplasmic reticulum-associated amyloid beta-peptide-binding protein 20669 Activities
Lysine-specific demethylase 4D-like 40243 Activities
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Huntingtin 19182 Activities
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Thyroid stimulating hormone receptor 29986 Activities
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Lysine-specific demethylase 4A 52245 Activities
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ATPase family AAA domain-containing protein 5 122566 Activities
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Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 93046 Activities
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Importin subunit beta-1/Snurportin-1 25097 Activities
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Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 36611 Activities
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Amyloid-beta A4 protein 8510 Activities
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Associated Targets(non-human)
GABA-A receptor; anion channel 5731 Activities
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P388 20296 Activities
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Escherichia coli 133304 Activities
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Bacillus subtilis 32866 Activities
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Pseudomonas aeruginosa 123386 Activities
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Candida albicans 78123 Activities
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Trichophyton mentagrophytes 4846 Activities
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Amorphotheca resinae 75 Activities
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Human alphaherpesvirus 1 11089 Activities
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Poliovirus 1 1274 Activities
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Plasmodium falciparum 966862 Activities
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Thioredoxin reductase 1, cytoplasmic 45279 Activities
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ATP-dependent Clp protease proteolytic subunit 20705 Activities
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Lipaphis erysimi 85 Activities
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Culex quinquefasciatus 137 Activities
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Cholinesterase 8742 Activities
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Acetylcholinesterase 12221 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: 244.29 | Molecular Weight (Monoisotopic): 244.1212 | AlogP: 1.92 | #Rotatable Bonds: 1 |
| Polar Surface Area: 54.12 | Molecular Species: NEUTRAL | HBA: 3 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 5.30 | CX LogP: 1.84 | CX LogD: 1.84 |
| Aromatic Rings: 2 | Heavy Atoms: 18 | QED Weighted: 0.75 | Np Likeness Score: 0.73 |
References
| 1. Cain M, Weber RW, Guzman F, Cook JM, Barker SA, Rice KC, Crawley JN, Paul SM, Skolnick P.. (1982) Beta-carbolines: synthesis and neurochemical and pharmacological actions on brain benzodiazepine receptors., 25 (9): [PMID:6127411] [10.1021/jm00351a015] |
| 2. Prinsep MR, Blunt JW, Munro MH.. (1991) New cytotoxic beta-carboline alkaloids from the marine bryozoan, Cribricellina cribraria., 54 (4): [PMID:1791472] [10.1021/np50076a023] |
| 3. PubChem BioAssay data set, |
| 4. Zeng Y, Zhang Y, Weng Q, Hu M, Zhong G.. (2010) Cytotoxic and insecticidal activities of derivatives of harmine, a natural insecticidal component isolated from Peganum harmala., 15 (11): [PMID:21060288] [10.3390/molecules15117775] |
| 5. Zhao Y, Ye F, Xu J, Liao Q, Chen L, Zhang W, Sun H, Liu W, Feng F, Qu W.. (2018) Design, synthesis and evaluation of novel bivalent β-carboline derivatives as multifunctional agents for the treatment of Alzheimer's disease., 26 (13): [PMID:29960728] [10.1016/j.bmc.2018.06.018] |
Source
Source(2):