Phallisin

HCID 115286CAS 19774-69-7
Substructure searchFind similar structures

Basic information

Standard SMILES
CC1NC(=O)C(CC(O)(CO)CO)NC(=O)C2Cc3c([nH]c4ccccc34)SCC(NC(=O)C(C(C)O)NC1=O)C(=O)N1CC(O)CC1C(=O)NC(C)C(=O)N2
InChIKey
SRDQDZSLNAKOIT-UHFFFAOYSA-N
Molecular formula
C35H48N8O12S
Average molar mass
804.9 g/mol
Monoisotopic mass
804.31123998

Overview

Phallisin has been reported in Amanita phalloides, Amanita bisporigera, and other organisms with data available.

Names & identifiers

Preferred name
Phallisin
IUPAC
28-[2,3-dihydroxy-2-(hydroxymethyl)propyl]-18-hydroxy-34-(1-hydroxyethyl)-23,31-dimethyl-12-thia-10,16,22,25,27,30,33,36-octazapentacyclo[12.11.11.03,11.04,9.016,20]hexatriaconta-3(11),4,6,8-tetraene-15,21,24,26,29,32,35-heptone
English name
phallisin
Molecular formula
C35H48N8O12S
Molecular weight
804.87

Names & synonyms

Phallisin19774-69-7DTXSID50104616128-[2,3-dihydroxy-2-(hydroxymethyl)propyl]-18-hydroxy-34-(1-hydroxyethyl)-23,31-dimethyl-12-thia-10,16,22,25,27,30,33,36-octazapentacyclo[12.11.11.03,11.04,9.016,20]hexatriaconta-3(11),4,6,8-tetraene-15,21,24,26,29,32,35-heptone28-(2,3-dihydroxy-2-(hydroxymethyl)propyl)-18-hydroxy-34-(1-hydroxyethyl)-23,31-dimethyl-12-thia-10,16,22,25,27,30,33,36-octazapentacyclo(12.11.11.03,11.04,9.016,20)hexatriaconta-3(11),4,6,8-tetraene-15,21,24,26,29,32,35-heptoneRefChem:172411DTXCID70152803028-(2,3-dihydroxy-2-(hydroxymethyl)propyl)-18,21,24,26,29,32,35-heptahydroxy-34-(1-hydroxyethyl)-23,31-dimethyl-12-thia-10,16,22,25,27,30,33,36-octaazapentacyclo(12.11.11.03,11.04,9.016,20)hexatriaconta-3(11),4,6,8,21,24,26,29,32,35-decaen-15-oneBRN 3028749PhallicinSCHEMBL2940369918,9-(Iminoethaniminoethaniminoethaniminomethano)-17H-pyrrolo(1',2':5,6)(1,5,8,11)thiatriazacyclopentadecino(15,14-b)indole-4,7,19,22,25,28,31(18H)-heptone,1,2,3,3a,5,6,8,9,10,15-decahydro-29-(2,3-dihydroxy-2-(hydroxymethyl)propyl)-6,26-dimethyl-2-hydroxy-23-(1-hydroxyethyl)-
Show more names
Phalloidin, 7-(4,5,5'-trihydroxy-L-leucine)-
XP181306NS00125401

Database identifiers

CAS
19774-69-7
PubChem CID
115286
DTXSID
DTXSID501046161

Properties

Computed structural properties

XLogP
-2.7
Topological polar surface area
337 Ų
Hydrogen bond donors
12
Hydrogen bond acceptors
13
Rotatable bonds
5
Heavy atoms
56

Physicochemical properties

Boiling point
1444.1 · 1444.1±65.0 °C(Predicted)
Density
1.55 · 1.55±0.1 g/cm3(Predicted)
pka
12.94 · 12.94±0.70(Predicted)

Safety & regulation

Toxicology

TreatmentConsider gastric lavage and activated charcoal. (A678)
Health EffectsLiver lesions, tachycardia, hypoglycemia, hypotension and electrolyte imbalance with acid- base disturbance (L1160).
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 item

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. (L1183, A2465)

Signs and Symptoms · 1 item

Hypovolemic shock; Gastrointestinal symptoms occur after a latent period and include abdominal pain, vomiting, and watery diarrhea. Neurologic symptoms are related to hepatic failure and may include encephalopathy, somnolence, confusion, coma and seizures (L1160).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemistry & industry

Uses & manufacturing

UsesPhalloin is one of a group of toxins from the death cap (Amanita phalloides) known as phallotoxins. (L996)

Suppliers2 total

如皋市天成化工有限公司/上海金成化工有限公司[email protected]
宝欧信特生物科技（苏州）有限公司51288865780 · [email protected]

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