Phallacidin
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Basic Info
| Common Name | Phallacidin(F04698) |
| 2D Structure | |
| Description | Phallacidin is one of a group of toxins from the death cap (Amanita phalloides) known as phallotoxins. The phallotoxins consist of at least seven compounds, all of which have seven similar peptide rings, isolated from the death cap (Amanita phalloides). (L996) |
| FRCD ID | F04698 |
| CAS Number | 26645-35-2 |
| PubChem CID | 44134886 |
| Formula | C37H50N8O13S |
| IUPAC Name | None |
| InChI Key | BYPSVXOZIRQBFU-UHFFFAOYSA-N |
| InChI | InChI=1S/C37H50N8O13S/c1-15(2)25-33(54)44-26(28(49)35(55)56)27(48)23-13-59-34-19(18-7-5-6-8-20(18)41-34)10-21(30(51)40-22(31(52)43-25)11-37(4,58)14-46)39-29(50)16(3)38-32(53)24-9-17(47)12-45(24)36(57)42-23/h5-8,15-17,21-26,28,41,46-47,49,58H,9-14H2,1-4H3,(H,38,53)(H,39,50)(H,40,51)(H,42,57)(H,43,52)(H,44,54)(H,55,56) |
| Canonical SMILES | CC1C(=O)NC2CC3=C(NC4=CC=CC=C34)SCC(C(=O)C(NC(=O)C(NC(=O)C(NC2=O)CC(C)(CO)O)C(C)C)C(C(=O)O)O)NC(=O)N5CC(CC5C(=O)N1)O |
| Isomeric SMILES | CC1C(=O)NC2CC3=C(NC4=CC=CC=C34)SCC(C(=O)C(NC(=O)C(NC(=O)C(NC2=O)CC(C)(CO)O)C(C)C)C(C(=O)O)O)NC(=O)N5CC(CC5C(=O)N1)O |
| Synonyms |
Cyclo[Ala-2-Mercapto-Trp-4,5-Dihydroxy-Leu-Val-erythro-3- Hydroxy-D -Asp-Cys-cis-4- Hydroxy-Pro]
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 846.91 |
| Hydrogen Bond Donor Count | 12 |
| Hydrogen Bond Acceptor Count | 14 |
| Rotatable Bond Count | 6 |
| Complexity | 1660 |
| Monoisotopic Mass | 846.322 |
| Exact Mass | 846.322 |
| XLogP | -1.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 59 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 10 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9863 |
| Human Intestinal Absorption | HIA+ | 0.6752 |
| Caco-2 Permeability | Caco2- | 0.7561 |
| P-glycoprotein Substrate | Substrate | 0.7839 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7688 |
| Non-inhibitor | 0.9788 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9512 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4786 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7406 |
| CYP450 2D6 Substrate | Non-substrate | 0.7383 |
| CYP450 3A4 Substrate | Substrate | 0.5436 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7146 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7256 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8799 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5947 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7764 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5981 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9962 |
| Non-inhibitor | 0.6962 | |
| AMES Toxicity | Non AMES toxic | 0.6848 |
| Carcinogens | Non-carcinogens | 0.7706 |
| Fish Toxicity | High FHMT | 0.9658 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9598 |
| Honey Bee Toxicity | Low HBT | 0.6771 |
| Biodegradation | Not ready biodegradable | 0.9959 |
| Acute Oral Toxicity | III | 0.5383 |
| Carcinogenicity (Three-class) | Non-required | 0.5510 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1744 | LogS |
| Caco-2 Permeability | 0.4653 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4503 | LD50, mol/kg |
| Fish Toxicity | 1.6515 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4021 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| A Simple and High-Throughput Analysis of Amatoxins and Phallotoxins in Human Plasma, Serum and Urine Using UPLC-MS/MS Combined with PRiME HLB μElution Platform. | Toxins (Basel) | 2016 May 4 | 27153089 |
| The molecular diversity of toxin gene families in lethal Amanita mushrooms. | Toxicon | 2014 Jun | 24613547 |
| A concept study on identification and attribution profiling of chemical threat agents using liquid chromatography-mass spectrometry applied to Amanita toxins in food. | Forensic Sci Int | 2012 Sep 10 | 22503887 |
Targets
- General Function:
- Myosin binding
- Specific Function:
- Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
- Gene Name:
- ACTC1
- Uniprot ID:
- P68032
- Molecular Weight:
- 42018.6 Da
- Mechanism of Action:
- Phallotoxins bind actin, preventing its depolymerization and poisoning the cell. They bind specifically at the interface between F-actin subunits, locking adjacent subunits together. This leads to a decrease in the rate constant for the dissociation of actin subunits from filament ends, which essentially stabilizes actin filaments through the prevention of filament depolymerization. Moreover, they inhibit the ATP hydrolysis activity of F-actin.
References
- Huang ZJ, Haugland RP, You WM, Haugland RP: Phallotoxin and actin binding assay by fluorescence enhancement. Anal Biochem. 1992 Jan;200(1):199-204. [1595896 ]
- General Function:
- Structural constituent of cytoskeleton
- Specific Function:
- Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
- Gene Name:
- ACTA1
- Uniprot ID:
- P68133
- Molecular Weight:
- 42050.67 Da
- Mechanism of Action:
- Phallotoxins bind actin, preventing its depolymerization and poisoning the cell. They bind specifically at the interface between F-actin subunits, locking adjacent subunits together. This leads to a decrease in the rate constant for the dissociation of actin subunits from filament ends, which essentially stabilizes actin filaments through the prevention of filament depolymerization. Moreover, they inhibit the ATP hydrolysis activity of F-actin.
References
- Huang ZJ, Haugland RP, You WM, Haugland RP: Phallotoxin and actin binding assay by fluorescence enhancement. Anal Biochem. 1992 Jan;200(1):199-204. [1595896 ]
- General Function:
- Protein kinase binding
- Specific Function:
- Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
- Gene Name:
- ACTA2
- Uniprot ID:
- P62736
- Molecular Weight:
- 42008.57 Da
- Mechanism of Action:
- Phallotoxins bind actin, preventing its depolymerization and poisoning the cell. They bind specifically at the interface between F-actin subunits, locking adjacent subunits together. This leads to a decrease in the rate constant for the dissociation of actin subunits from filament ends, which essentially stabilizes actin filaments through the prevention of filament depolymerization. Moreover, they inhibit the ATP hydrolysis activity of F-actin.
References
- Huang ZJ, Haugland RP, You WM, Haugland RP: Phallotoxin and actin binding assay by fluorescence enhancement. Anal Biochem. 1992 Jan;200(1):199-204. [1595896 ]
- General Function:
- Tat protein binding
- Specific Function:
- Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
- Gene Name:
- ACTB
- Uniprot ID:
- P60709
- Molecular Weight:
- 41736.37 Da
- Mechanism of Action:
- Phallotoxins bind actin, preventing its depolymerization and poisoning the cell. They bind specifically at the interface between F-actin subunits, locking adjacent subunits together. This leads to a decrease in the rate constant for the dissociation of actin subunits from filament ends, which essentially stabilizes actin filaments through the prevention of filament depolymerization. Moreover, they inhibit the ATP hydrolysis activity of F-actin.
References
- Huang ZJ, Haugland RP, You WM, Haugland RP: Phallotoxin and actin binding assay by fluorescence enhancement. Anal Biochem. 1992 Jan;200(1):199-204. [1595896 ]
- General Function:
- Ubiquitin protein ligase binding
- Specific Function:
- Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
- Gene Name:
- ACTG1
- Uniprot ID:
- P63261
- Molecular Weight:
- 41792.48 Da
- Mechanism of Action:
- Phallotoxins bind actin, preventing its depolymerization and poisoning the cell. They bind specifically at the interface between F-actin subunits, locking adjacent subunits together. This leads to a decrease in the rate constant for the dissociation of actin subunits from filament ends, which essentially stabilizes actin filaments through the prevention of filament depolymerization. Moreover, they inhibit the ATP hydrolysis activity of F-actin.
References
- Huang ZJ, Haugland RP, You WM, Haugland RP: Phallotoxin and actin binding assay by fluorescence enhancement. Anal Biochem. 1992 Jan;200(1):199-204. [1595896 ]
- General Function:
- Atp binding
- Specific Function:
- Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
- Gene Name:
- ACTG2
- Uniprot ID:
- P63267
- Molecular Weight:
- 41876.495 Da
- Mechanism of Action:
- Phallotoxins bind actin, preventing its depolymerization and poisoning the cell. They bind specifically at the interface between F-actin subunits, locking adjacent subunits together. This leads to a decrease in the rate constant for the dissociation of actin subunits from filament ends, which essentially stabilizes actin filaments through the prevention of filament depolymerization. Moreover, they inhibit the ATP hydrolysis activity of F-actin.
References
- Huang ZJ, Haugland RP, You WM, Haugland RP: Phallotoxin and actin binding assay by fluorescence enhancement. Anal Biochem. 1992 Jan;200(1):199-204. [1595896 ]