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PIRLINDOLE
ID: ALA32350
Max Phase: Phase
Molecular Formula: C15H18N2
Molecular Weight: 226.32
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (2): Pirazidol | Pirlindole
Synonyms from Alternative Forms(2):
Canonical SMILES: Cc1ccc2c(c1)c1c3n2CCNC3CCC1
Standard InChI: InChI=1S/C15H18N2/c1-10-5-6-14-12(9-10)11-3-2-4-13-15(11)17(14)8-7-16-13/h5-6,9,13,16H,2-4,7-8H2,1H3
Standard InChI Key: IWVRVEIKCBFZNF-UHFFFAOYSA-N
Associated Targets(Human)
HeLa 62764 Activities
Transcriptional enhancer factor TEF-1 34 Activities
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Transcriptional enhancer factor TEF-4 30 Activities
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Transcriptional enhancer factor TEF-5 23 Activities
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Transcriptional enhancer factor TEF-3 237 Activities
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MCF7 126967 Activities
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Serum response factor 1 Activities
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Histone deacetylase 6 20808 Activities
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|---|
Dopamine D1 receptor 9720 Activities
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HERG 29587 Activities
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Dopamine transporter 10535 Activities
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|---|
Estrogen receptor alpha 17718 Activities
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|---|
Acetylcholinesterase 18204 Activities
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|---|
Norepinephrine transporter 10102 Activities
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|---|
Serotonin transporter 12625 Activities
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|---|
Alpha-2a adrenergic receptor 9450 Activities
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|---|
Mu opioid receptor 19785 Activities
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|---|
Monoamine oxidase A 11911 Activities
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Serotonin 1a (5-HT1a) receptor 14969 Activities
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|---|
Vascular endothelial growth factor receptor 2 20924 Activities
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|---|
Phosphodiesterase 3A 3309 Activities
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|---|
Dopamine D3 receptor 14368 Activities
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|---|
Muscarinic acetylcholine receptor M2 10671 Activities
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Thrombin 11687 Activities
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Thromboxane A2 receptor 5717 Activities
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Adenosine A3 receptor 15931 Activities
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Histamine H3 receptor 10389 Activities
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Serotonin 2b (5-HT2b) receptor 10323 Activities
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Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 1034 Activities
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Androgen Receptor 11781 Activities
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Progesterone receptor 8562 Activities
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Cyclooxygenase-1 9233 Activities
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Phosphodiesterase 4A 1943 Activities
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Alpha-1a adrenergic receptor 8359 Activities
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Muscarinic acetylcholine receptor M1 12690 Activities
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Associated Targets(non-human)
GABA-A receptor; anion channel 5731 Activities
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Trypanosoma cruzi 99888 Activities
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Trypanosoma brucei rhodesiense 7991 Activities
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Trypanosoma brucei brucei 13300 Activities
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Trypanosoma brucei 78846 Activities
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Trichomonas vaginalis 2376 Activities
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Toxoplasma gondii 4585 Activities
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Pneumocystis carinii 749 Activities
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Plasmodium falciparum 966862 Activities
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Leishmania mexicana 936 Activities
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Leishmania major 2877 Activities
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Leishmania infantum 5912 Activities
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Leishmania donovani 89745 Activities
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Leishmania amazonensis 3813 Activities
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Entamoeba histolytica 2676 Activities
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Cryptosporidium parvum 1150 Activities
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SARS-CoV-2 38078 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 |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Properties
| Molecular Weight: 226.32 | Molecular Weight (Monoisotopic): 226.1470 | AlogP: 2.93 | #Rotatable Bonds: 0 |
| Polar Surface Area: 16.96 | Molecular Species: BASE | HBA: 2 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 2 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 8.70 | CX LogP: 3.10 | CX LogD: 1.79 |
| Aromatic Rings: 2 | Heavy Atoms: 17 | QED Weighted: 0.73 | Np Likeness Score: -0.20 |
References
| 1. Chebib M, Johnston GA.. (2000) GABA-Activated ligand gated ion channels: medicinal chemistry and molecular biology., 43 (8): [PMID:10780899] [10.1021/jm9904349] |
| 2. Prado-Prado FJ, García-Mera X, González-Díaz H.. (2010) Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species., 18 (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068] |
| 3. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, |
| 4. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson. (2020) Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2, [10.1101/2020.04.21.054387] |
| 5. Smith SA, Sessions RB, Shoemark DK, Williams C, Ebrahimighaei R, McNeill MC, Crump MP, McKay TR, Harris G, Newby AC, Bond M.. (2019) Antiproliferative and Antimigratory Effects of a Novel YAP-TEAD Interaction Inhibitor Identified Using in Silico Molecular Docking., 62 (3): [PMID:30640473] [10.1021/acs.jmedchem.8b01402] |
| 6. Ellen Van Damme. (2021) Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity, [10.6019/CHEMBL4651402] |
| 7. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius. (2021) HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators, [10.6019/CHEMBL4808148] |
| 8. Sutherland JJ, Yonchev D, Fekete A, Urban L.. (2023) A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs., 14 (1): [PMID:37468498] [10.1038/s41467-023-40064-9] |
Source
Source(5):