Phallacin
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Basic Info
| Common Name | Phallacin(F04699) |
| 2D Structure | |
| Description | Phallacin 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 | F04699 |
| CAS Number | 53568-40-4 |
| PubChem CID | 171277 |
| Formula | C37H50N8O12S |
| IUPAC Name | None |
| InChI Key | LAVFLHFIXHMDLZ-UHFFFAOYSA-N |
| InChI | InChI=1S/C37H50N8O12S/c1-15(2)25-32(52)44-26(27(47)36(55)56)33(53)41-23-14-58-34-19(18-8-6-7-9-20(18)42-34)11-21(29(49)40-22(30(50)43-25)12-37(4,5)57)39-28(48)16(3)38-31(51)24-10-17(46)13-45(24)35(23)54/h6-9,15-17,21-27,42,46-47,57H,10-14H2,1-5H3,(H,38,51)(H,39,48)(H,40,49)(H,41,53)(H,43,50)(H,44,52)(H,55,56) |
| Canonical SMILES | CC1C(=O)NC2CC3=C(NC4=CC=CC=C34)SCC(C(=O)N5CC(CC5C(=O)N1)O)NC(=O)C(NC(=O)C(NC(=O)C(NC2=O)CC(C)(C)O)C(C)C)C(C(=O)O)O |
| Isomeric SMILES | CC1C(=O)NC2CC3=C(NC4=CC=CC=C34)SCC(C(=O)N5CC(CC5C(=O)N1)O)NC(=O)C(NC(=O)C(NC(=O)C(NC2=O)CC(C)(C)O)C(C)C)C(C(=O)O)O |
| Synonyms |
Phallacin
Phallacidin, 3-(4-hydroxy-L-leucine)-
AC1L577N
53568-40-4
LS-102542
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Peptides |
| Direct Parent | Oligopeptides |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Alpha-oligopeptide - Cyclic alpha peptide - Macrolactam - 3-alkylindole - Alpha-amino acid or derivatives - Indole - Indole or derivatives - Aryl thioether - Alkylarylthioether - Hydroxy acid - Benzenoid - Alpha-hydroxy acid - Heteroaromatic compound - Tertiary alcohol - Pyrrolidine - Pyrrole - Tertiary carboxylic acid amide - Carboxamide group - Lactam - Secondary carboxylic acid amide - Secondary alcohol - Monocarboxylic acid or derivatives - Organoheterocyclic compound - Azacycle - Carboxylic acid - Thioether - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Alcohol - Carbonyl group - Organooxygen compound - Organic oxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 830.911 |
| Hydrogen Bond Donor Count | 11 |
| Hydrogen Bond Acceptor Count | 13 |
| Rotatable Bond Count | 5 |
| Complexity | 1630 |
| Monoisotopic Mass | 830.327 |
| Exact Mass | 830.327 |
| XLogP | -0.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 58 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 9 |
| 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- | 0.9917 |
| Human Intestinal Absorption | HIA- | 0.6159 |
| Caco-2 Permeability | Caco2- | 0.7709 |
| P-glycoprotein Substrate | Substrate | 0.8212 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7288 |
| Non-inhibitor | 0.9374 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9505 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4712 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8118 |
| CYP450 2D6 Substrate | Non-substrate | 0.7221 |
| CYP450 3A4 Substrate | Substrate | 0.5933 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7671 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7877 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8914 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6602 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8960 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7054 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9988 |
| Non-inhibitor | 0.7401 | |
| AMES Toxicity | Non AMES toxic | 0.7862 |
| Carcinogens | Non-carcinogens | 0.8345 |
| Fish Toxicity | High FHMT | 0.9800 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9628 |
| Honey Bee Toxicity | Low HBT | 0.6764 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.5741 |
| Carcinogenicity (Three-class) | Non-required | 0.5721 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.0330 | LogS |
| Caco-2 Permeability | 0.2216 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.5345 | LD50, mol/kg |
| Fish Toxicity | 1.5640 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3909 | pIGC50, ug/L |
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 ]