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MONOCROTALINE
ID: ALA521035
Max Phase: Preclinical
Molecular Formula: C16H23NO6
Molecular Weight: 325.36
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): Monocrotaline
Synonyms from Alternative Forms(1):
Canonical SMILES: C[C@H]1C(=O)O[C@@H]2CCN3CC=C(COC(=O)[C@](C)(O)[C@]1(C)O)[C@H]23
Standard InChI: InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1
Standard InChI Key: QVCMHGGNRFRMAD-XFGHUUIASA-N
Associated Targets(Human)
A204 242 Activities
KB 17409 Activities
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Thyroid hormone receptor beta-1 7926 Activities
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Geminin 128009 Activities
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Cellular tumor antigen p53 48468 Activities
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Tyrosyl-DNA phosphodiesterase 1 345557 Activities
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Solute carrier organic anion transporter family member 1B1 2672 Activities
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Solute carrier organic anion transporter family member 1B3 2517 Activities
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Associated Targets(non-human)
Human immunodeficiency virus type 1 reverse transcriptase 18245 Activities
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Beta-lactamase AmpC 62480 Activities
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Acetylcholinesterase 12221 Activities
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Cholinesterase 8742 Activities
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Lactuca sativa 1092 Activities
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CHO 4503 Activities
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Spodoptera littoralis 798 Activities
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Rhopalosiphum padi 121 Activities
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Myzus persicae 1112 Activities
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Leptinotarsa decemlineata 1161 Activities
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Meloidogyne incognita 862 Activities
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Rhabditis sp. 25 Activities
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Pratylenchus penetrans 14 Activities
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Heterodera schachtii 22 Activities
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Phasmarhabditis hermaphrodita 5 Activities
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Rattus norvegicus 775804 Activities
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SARS-CoV-2 38078 Activities
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Escherichia coli 133304 Activities
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Pseudomonas aeruginosa 123386 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: 325.36 | Molecular Weight (Monoisotopic): 325.1525 | AlogP: -0.39 | #Rotatable Bonds: 0 |
| Polar Surface Area: 96.30 | Molecular Species: NEUTRAL | HBA: 7 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 11.49 | CX Basic pKa: 8.08 | CX LogP: -0.33 | CX LogD: -1.10 |
| Aromatic Rings: 0 | Heavy Atoms: 23 | QED Weighted: 0.46 | Np Likeness Score: 2.65 |
References
| 1. Perdue RE.. (1982) KB cell culture I. Role in discovery of antitumor agents from higher plants., 45 (4): [PMID:7130986] [10.1021/np50022a010] |
| 2. Zalkow LH, Asibal CF, Glinski JA, Bonetti SJ, Gelbaum LT, VanDerveer D, Powis G.. (1988) Macrocyclic pyrrolizidine alkaloids from Senecio anonymus. Separation of a complex alkaloid extract using droplet counter-current chromatography., 51 (4): [PMID:3210016] [10.1021/np50058a005] |
| 3. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH.. (1991) Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase., 54 (1): [PMID:1710653] [10.1021/np50073a012] |
| 4. PubChem BioAssay data set, |
| 5. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ.. (2010) Developing structure-activity relationships for the prediction of hepatotoxicity., 23 (7): [PMID:20553011] [10.1021/tx1000865] |
| 6. Ekins S, Williams AJ, Xu JJ.. (2010) A predictive ligand-based Bayesian model for human drug-induced liver injury., 38 (12): [PMID:20843939] [10.1124/dmd.110.035113] |
| 7. PubChem BioAssay data set, |
| 8. PubChem BioAssay data set, |
| 9. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P.. (2012) Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine., 20 (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040] |
| 10. (2008) 36 (3): [10.1016/jbse.2007.08.015] |
| 11. Thoden TC, Boppré M, Hallmann J.. (2009) Effects of pyrrolizidine alkaloids on the performance of plant-parasitic and free-living nematodes., 65 (7): [PMID:19378265] [10.1002/ps.1764] |
| 12. Unpublished dataset, |
| 13. Unpublished dataset, |
| 14. Unpublished dataset, |
| 15. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP.. (2013) Structure-based identification of OATP1B1/3 inhibitors., 83 (6): [PMID:23571415] [10.1124/mol.112.084152] |
| 16. PubChem BioAssay data set, |
| 17. PubChem BioAssay data set, |
| 18. PubChem BioAssay data set, |
| 19. Open TG-GATES, [10.6019/CHEMBL3885861] |
| 20. DrugMatrix, [10.6019/CHEMBL3885881] |
| 21. Ellen Van Damme. (2021) Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity, [10.6019/CHEMBL4651402] |
| 22. Dematei A, Nunes JB, Moreira DC, Jesus JA, Laurenti MD, Mengarda ACA, Vieira MS, do Amaral CP, Domingues MM, de Moraes J, Passero LFD, Brand G, Bessa LJ, Wimmer R, Kuckelhaus SAS, Tomás AM, Santos NC, Plácido A, Eaton P, Leite JRSA.. (2021) Mechanistic Insights into the Leishmanicidal and Bactericidal Activities of Batroxicidin, a Cathelicidin-Related Peptide from a South American Viper (Bothrops atrox)., 84 (6.0): [PMID:34077221] [10.1021/acs.jnatprod.1c00153] |
Source
Source(6):