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Phalloidin information


Phalloidin
Identifiers
CAS Number
  • 17466-45-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:8040 ☒N
ChemSpider
  • 28467534 ☒N
ECHA InfoCard 100.037.697 Edit this at Wikidata
PubChem CID
  • 441542
UNII
  • 5A520O87TI checkY
CompTox Dashboard (EPA)
  • DTXSID3037254 Edit this at Wikidata
InChI
  • InChI=1S/C35H48N8O11S/c1-15-27(47)38-22-10-20-19-7-5-6-8-21(19)41-33(20)55-13-24(34(53)43-12-18(46)9-25(43)31(51)37-15)40-32(52)26(17(3)45)42-28(48)16(2)36-30(50)23(39-29(22)49)11-35(4,54)14-44/h5-8,15-18,22-26,41,44-46,54H,9-14H2,1-4H3,(H,36,50)(H,37,51)(H,38,47)(H,39,49)(H,40,52)(H,42,48)/t15-,16?,17-,18+,22-,23-,24+,25-,26+,35+/m0/s1 ☒N
    Key: KPKZJLCSROULON-RCGKFKHASA-N ☒N
  • InChI=1/C35H48N8O11S/c1-15-27(47)38-22-10-20-19-7-5-6-8-21(19)41-33(20)55-13-24(34(53)43-12-18(46)9-25(43)31(51)37-15)40-32(52)26(17(3)45)42-28(48)16(2)36-30(50)23(39-29(22)49)11-35(4,54)14-44/h5-8,15-18,22-26,41,44-46,54H,9-14H2,1-4H3,(H,36,50)(H,37,51)(H,38,47)(H,39,49)(H,40,52)(H,42,48)/t15-,16?,17-,18+,22-,23-,24+,25-,26+,35+/m0/s1
    Key: KPKZJLCSROULON-RCGKFKHABO
SMILES
  • C[C@H]1C(=O)N[C@H]2Cc3c4ccccc4[nH]c3SC[C@H](C(=O)N5C[C@@H](C[C@H]5C(=O)N1)O)NC(=O)[C@H](NC(=O)C(NC(=O)[C@@H](NC2=O)C[C@](C)(CO)O)C)[C@H](C)O
Properties
Chemical formula
C35H48N8O11S
Molar mass 788.87 g·mol−1
Appearance Needles
Melting point 281 °C (538 °F; 554 K) (hyd)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Phalloidin belongs to a class of toxins called phallotoxins, which are found in the death cap mushroom (Amanita phalloides). It is a rigid bicyclic heptapeptide that is lethal after a few days when injected into the bloodstream. The major symptom of phalloidin poisoning is acute hunger due to the destruction of liver cells. It functions by binding and stabilizing filamentous actin (F-actin) and effectively prevents the depolymerization of actin fibers. Due to its tight and selective binding to F-actin, derivatives of phalloidin containing fluorescent tags are used widely in microscopy to visualize F-actin in biomedical research.

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Phalloidin

Last Update:

Phalloidin belongs to a class of toxins called phallotoxins, which are found in the death cap mushroom (Amanita phalloides). It is a rigid bicyclic heptapeptide...

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Phallotoxin

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residue smaller, both in the final product and the precursor protein. Phalloidin had been isolated in 1937 by Feodor Lynen, Heinrich Wieland's student...

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LifeAct Dye

Last Update:

Actin probe, Acti-stain 488 phalloidin, Acti-stain 555 phalloidin, Acti-stain 535 phalloidin, Acti-stain 670 phalloidin, Actin stain, Actin -stain488"...

Word Count : 724

Fluorescence microscope

Last Update:

fluorescent reporter. A major example of this class of fluorescent stain is phalloidin, which is used to stain actin fibers in mammalian cells. A new peptide...

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Cytoskeletal drugs

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of the cytoskeleton, such as taxol, which stabilizes microtubules, or Phalloidin, which stabilizes actin filaments. Others, such as Cytochalasin D, bind...

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Epididymis

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These filaments have been visualized at high resolution using fluorescent phalloidin that binds to actin filaments. The stereocilia in the epididymis are non-motile...

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Amanita phalloides

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least seven compounds, all of which have seven similar peptide rings. Phalloidin was isolated in 1937 by Feodor Lynen, Heinrich Wieland's student and son-in-law...

Word Count : 6619

Amatoxin

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structure has not been determined. Amanitin is very closely related to phalloidins, which are bicyclic 7-residue toxins. They both are part of the MSDIN...

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Amanita virosa

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least seven compounds, all of which have seven similar peptide rings. Phalloidin was isolated in 1937 by Feodor Lynen, Heinrich Wieland's student and son-in-law...

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Fish

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Gliotoxin Ibotenic acid Lolitrem B Muscimol Orellanine Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins...

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Antamanide

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It is being studied as a potential anti-toxin against the effects of phalloidin and for its potential for treating edema. It contains 1 valine residue...

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Hydroxyproline

Last Update:

is found in the toxic cyclic peptides from Amanita mushrooms (e.g., phalloidin). Secondary amino acid Imino acid Hydroxylysine R.H.A. Plimmer (1912)...

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Oligopeptide

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the HIV envelope sequence required for attachment to the CD4 receptor. Phalloidin - A very toxic polypeptide isolated mainly from Amanita phalloides (Agaricaceae)...

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HeLa

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fluorescence image of HeLa cells stained with the actin- binding toxin phalloidin (red), microtubules (cyan), and cell nuclei (blue). Nikon RTS2000MP custom...

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Clostridium botulinum

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Gliotoxin Ibotenic acid Lolitrem B Muscimol Orellanine Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins...

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PC3

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Actin (Phalloidin) and Nuclei (DAPI) staining...

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Actin

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can be observed under the microscope thanks to fluorophore-conjugated phalloidin staining. In somatic cell nuclei, however, actin filaments cannot be observed...

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Tuft cell

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free-floating DDY mouse jejunum (green: phospho-Girdin at tyrosine 1798, red: phalloidin, blue: DAPI) prepared by Iida M, Tanaka M, Asai M in Institute for Developmental...

Word Count : 1840

Fluorophore

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mitochondria stained red with MitoTracker Red CMXRos, and F-actin stained green with Alexa Fluor 488 phalloidin and imaged on a fluorescent microscope....

Word Count : 2024

Botulinum toxin

Last Update:

Gliotoxin Ibotenic acid Lolitrem B Muscimol Orellanine Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins...

Word Count : 11720

Poison dart frog

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Gliotoxin Ibotenic acid Lolitrem B Muscimol Orellanine Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins...

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Tetrodotoxin

Last Update:

Gliotoxin Ibotenic acid Lolitrem B Muscimol Orellanine Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins...

Word Count : 6817

Exotoxin

Last Update:

Gliotoxin Ibotenic acid Lolitrem B Muscimol Orellanine Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins...

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Ricin

Last Update:

Gliotoxin Ibotenic acid Lolitrem B Muscimol Orellanine Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins...

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Plasmodesma

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tobacco leaves are treated with a drug that stabilizes actin filaments, phalloidin, the cucumber mosaic virus movement proteins are unable to increase the...

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Ciguatera fish poisoning

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Gliotoxin Ibotenic acid Lolitrem B Muscimol Orellanine Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins...

Word Count : 3418

Tetanus toxin

Last Update:

Gliotoxin Ibotenic acid Lolitrem B Muscimol Orellanine Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins...

Word Count : 2351

Shiga toxin

Last Update:

Gliotoxin Ibotenic acid Lolitrem B Muscimol Orellanine Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins...

Word Count : 2259

Snake venom

Last Update:

Gliotoxin Ibotenic acid Lolitrem B Muscimol Orellanine Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins...

Word Count : 7592

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