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ALTERTOXIN I
ID: ALA521470
Max Phase: Preclinical
Molecular Formula: C20H16O6
Molecular Weight: 352.34
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): Altertoxin I
Synonyms from Alternative Forms(1):
Canonical SMILES: O=C1C[C@H](O)[C@@H]2c3c(ccc(O)c31)-c1ccc(O)c3c1[C@@]2(O)CCC3=O
Standard InChI: InChI=1S/C20H16O6/c21-10-3-1-8-9-2-4-11(22)17-12(23)5-6-20(26,18(9)17)19-14(25)7-13(24)16(10)15(8)19/h1-4,14,19,21-22,25-26H,5-7H2/t14-,19+,20-/m0/s1
Standard InChI Key: GJIALGLHOBXNAT-KPOBHBOGSA-N
Associated Targets(Human)
Serine/threonine-protein kinase AKT 9192 Activities
NUAK family SNF1-like kinase 1 1769 Activities
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Serine/threonine-protein kinase Aurora-A 10240 Activities
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Serine/threonine-protein kinase Aurora-B 6805 Activities
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Serine/threonine-protein kinase B-raf 11587 Activities
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Cyclin-dependent kinase 4/cyclin D1 2340 Activities
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Mitogen-activated protein kinase kinase kinase 8 459 Activities
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Epidermal growth factor receptor erbB1 33727 Activities
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Ephrin type-B receptor 4 3198 Activities
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Cyclin-dependent kinase 2 9050 Activities
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Receptor protein-tyrosine kinase erbB-2 7851 Activities
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Focal adhesion kinase 1 4730 Activities
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Insulin-like growth factor I receptor 8605 Activities
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Tyrosine-protein kinase SRC 10310 Activities
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Vascular endothelial growth factor receptor 2 20924 Activities
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Vascular endothelial growth factor receptor 3 3216 Activities
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Tyrosine-protein kinase receptor FLT3 13481 Activities
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Insulin receptor 5558 Activities
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Hepatocyte growth factor receptor 10718 Activities
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Platelet-derived growth factor receptor beta 5195 Activities
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Serine/threonine-protein kinase PLK1 28605 Activities
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Casein kinase II alpha 3512 Activities
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Serine/threonine-protein kinase PLK4 1882 Activities
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Tyrosine-protein kinase TIE-2 3348 Activities
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Telomerase reverse transcriptase 2428 Activities
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HeLa 62764 Activities
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A549 127892 Activities
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HCT-116 91556 Activities
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Associated Targets(non-human)
L5178Y 1809 Activities
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Escherichia coli 133304 Activities
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Klebsiella pneumoniae 43867 Activities
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Pseudomonas aeruginosa 123386 Activities
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Acinetobacter baumannii 41033 Activities
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Pichia kudriavzevii 7448 Activities
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Aspergillus fumigatus 16427 Activities
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Staphylococcus aureus 210822 Activities
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Streptococcus pneumoniae 31063 Activities
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Enterococcus faecium 13803 Activities
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Enterobacter cloacae 7976 Activities
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Aspergillus ficuum 42 Activities
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Candida albicans 78123 Activities
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Human immunodeficiency virus 1 70413 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 |
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Properties
| Molecular Weight: 352.34 | Molecular Weight (Monoisotopic): 352.0947 | AlogP: 1.97 | #Rotatable Bonds: 0 |
| Polar Surface Area: 115.06 | Molecular Species: NEUTRAL | HBA: 6 | HBD: 4 |
| #RO5 Violations: 0 | HBA (Lipinski): 6 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 8.24 | CX Basic pKa: | CX LogP: 1.88 | CX LogD: 1.82 |
| Aromatic Rings: 2 | Heavy Atoms: 26 | QED Weighted: 0.58 | Np Likeness Score: 2.08 |
References
| 1. Aly AH, Edrada-Ebel R, Indriani ID, Wray V, Müller WE, Totzke F, Zirrgiebel U, Schächtele C, Kubbutat MH, Lin WH, Proksch P, Ebel R.. (2008) Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense., 71 (6): [PMID:18494522] [10.1021/np070447m] |
| 2. Kjer J, Wray V, Edrada-Ebel R, Ebel R, Pretsch A, Lin W, Proksch P.. (2009) Xanalteric acids I and II and related phenolic compounds from an endophytic Alternaria sp. isolated from the mangrove plant Sonneratia alba., 72 (11): [PMID:19835393] [10.1021/np900417g] |
| 3. Chen JL, Sperry J, Ip NY, Brimble MA. (2011) Natural products targeting telomere maintenance, 2 (4): [10.1039/C0MD00241K] |
| 4. Bashyal BP, Wellensiek BP, Ramakrishnan R, Faeth SH, Ahmad N, Gunatilaka AA.. (2014) Altertoxins with potent anti-HIV activity from Alternaria tenuissima QUE1Se, a fungal endophyte of Quercus emoryi., 22 (21): [PMID:25260957] [10.1016/j.bmc.2014.08.039] |
| 5. Zhao DL, Cao F, Wang CY, Yang LJ, Shi T, Wang KL, Shao CL, Wang CY.. (2019) Alternatone A, an Unusual Perylenequinone-Related Compound from a Soft-Coral-Derived Strain of the Fungus Alternaria alternata., 82 (11): [PMID:31659905] [10.1021/acs.jnatprod.9b00905] |
| 6. Geris R, Pinho MA, Boffo EF, Simpson TJ.. (2022) Naturally Occurring Partially Reduced Perylenequinones from Fungi., 85 (9.0): [PMID:36098709] [10.1021/acs.jnatprod.2c00368] |
Source
Source(1):