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Merck
CN

P8157

Sigma-Aldrich

Phallacidin from Amanita phalloides

≥85%

Synonym(s):

Cyclo(Ala-2-Mercapto-Trp-4,5-Dihydroxy-Leu-Val-erythro-3-Hydroxy-D-Asp-Cys-cis-4-Hydroxy-Pro)

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About This Item

Empirical Formula (Hill Notation):
C37H50N8O13S
CAS Number:
26645-35-2
Molecular Weight:
846.90
MDL number:
MFCD00063359
UNSPSC Code:
12352202
PubChem Substance ID:
24898913
NACRES:
NA.56

Key Documents

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biological source

Amanita phalloides

Assay

≥85%

form

powder

SMILES string

CC(C)C1NC(=O)C(CC(C)(O)CO)NC(=O)C2Cc3c(SCC(NC(=O)C(NC1=O)C(O)C(O)=O)C(=O)N4CC(O)CC4C(=O)NC(C)C(=O)N2)[nH]c5ccccc35

InChI

1S/C37H50N8O13S/c1-15(2)25-32(53)44-26(27(48)36(56)57)33(54)41-23-13-59-34-19(18-7-5-6-8-20(18)42-34)10-21(29(50)40-22(30(51)43-25)11-37(4,58)14-46)39-28(49)16(3)38-31(52)24-9-17(47)12-45(24)35(23)55/h5-8,15-17,21-27,42,46-48,58H,9-14H2,1-4H3,(H,38,52)(H,39,49)(H,40,50)(H,41,54)(H,43,51)(H,44,53)(H,56,57)

InChI key

KUBDTFZQCYLLGC-UHFFFAOYSA-N

Biochem/physiol Actions

Phallacidin, which is a bicyclic toxin from the Amanita phalloides mushroom, has been shown to inhibit F-actin degradation by proteolytic enzymes including trypsin and α-chymotrypsin.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBW7748
SLBV1815
SLBN7513V
SLBM8365V
SLBM1526V

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K Barber et al.
Neuroscience letters, 207(1), 17-20 (1996-03-22)
Use of fluorescent probes to monitor f-actin in living cells typically relies on difficult microinjection procedures. The current work has developed cationic lipotransfer of membrane-impermeant probes as an alternative to microinjection. BODIPY FL-phallacidin, a fluorescent f-actin probe, was packaged into
Samantha J Pitt et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 28(45), 11454-11467 (2008-11-07)
The time course of currents mediated by native and recombinant glycine receptors was examined with a combination of rapid agonist applications to outside-out patches and single-channel recording. The deactivation time constant of currents evoked by brief, saturating pulses of glycine
J W Semple et al.
British journal of haematology, 97(4), 747-754 (1997-06-01)
The pathophysiology of platelet dysfunction in the Wiskott-Aldrich immune deficiency syndrome (WAS) remains unclear. Using flow cytometry, we have characterized the functional properties of platelets from 10 children with WAS. Patients with WAS had thrombocytopenia, small platelets, increased platelet-associated IgG
Rachel E Laudadio et al.
American journal of physiology. Cell physiology, 289(6), C1388-C1395 (2005-08-27)
Although changes of cytoskeleton (CSK) stiffness and friction can be induced by diverse interventions, all mechanical changes reported to date can be scaled onto master relationships that appear to be universal. To assess the limits of the applicability of those
J de Vries et al.
Biochemistry, 17(10), 1965-1968 (1978-05-16)
The rate of proteolytic degradation of rabbit skeletal muscle actin by trypsin, alpha-chymotrypsin, and, mainly, subtilisin was followed by dual wavelength spectroscopy at 285 nm by reference at 320 nm. Phalloidin and phallacidin, two toxic bicyclic heptapeptides from the mushroom
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