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Calotoxin

HCID 56840852
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Grundinformationen

CAS
20304-49-8
Standard-SMILES
C[C@H]1O[C@H]2O[C@@H]3C[C@@H]4CC[C@@H]5C(CC[C@]6(C)[C@@H](C7=CC(=O)OC7)CC[C@]56O)[C@@]4(C=O)C[C@H]3O[C@@]2(O)[C@H](O)[C@@H]1O
InChIKey
LYSHVSOMKBORDM-LQHZDSTDSA-N
Summenformel
C29H40O10
Durchschnittliche Molmasse
548,6 g/mol
Monoisotopische Masse
548,26214747

Überblick

calotoxin has been reported in Asclepias, Danaus genutia, and other organisms with data available.

Namen und Bezeichner

Bevorzugter Name
Calotoxin
IUPAC
(1S,3R,5S,7R,8S,9R,10S,12R,14R,18R,19R,22S,23R)-8,9,10,22-tetrahydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde

Namen und Synonyme

CALOTOXINHSDB 3468BRN 0072512DTXSID401741934-18-00-03126 (Beilstein Handbook Reference)20304-49-85-alpha-Card-20(22)-enolide, 3-beta-((6-deoxy-beta-D-hexopyranos-2-ulos-1-yl)oxy)2-alpha,14-dihydroxy-19-oxo-Card-20(22)-enolide, 3-((6-deoxy-beta-D-hexopyranos-2-ulos-1-yl)oxy)-2,14-dihydroxy-19-oxo-,(2alpha,3beta,5alpha)-5-alpha-Card-20(22)-enolide, 3-beta-((6-deoxy-beta-D-hexopyranos-2-ulos-1-yl)oxy)-2-alpha,14-dihydroxy-19-oxo-(1S,3R,5S,7R,8S,9R,10S,12R,14R,18R,19R,22S,23R)-8,9,10,22-tetrahydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo(12.11.0.03,12.05,10.015,23.018,22)pentacosane-14-carbaldehyde(1S,3R,5S,7R,8S,9R,10S,12R,14R,18R,19R,22S,23R)-8,9,10,22-tetrahydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehydeRefChem:123040
Weitere Namen anzeigen
DTXCID10966845alphaCard20(22)enolide, 3beta((6deoxybetaDhexopyranos2ulos1yl)oxy)2alpha,14dihydroxy19oxoCARD-20(22)-ENOLIDE, 3-((6-DEOXY-BETA-D-HEXOPYRANOS-2-ULOS-1-YL)OXY)-2,14-DIHYDROXY-19-OXO-, (2ALPHA,3BETA,5ALPHA)-Card20(22)enolide, 3((6deoxybetaDhexopyranos2ulos1yl)oxy)2,14dihydroxy19oxo,(2alpha,3beta,5alpha)8,9,10,22-tetrahydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo(12.11.0.03,12.05,10.015,23.018,22)pentacosane-14-carbaldehyde8,9,10,22-tetrahydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehydeSCHEMBL29389118(1R,3aS,3bR,5aS,6aR,7aS,9R,10S,11R,11aS,12aR,13aR,15aR)-3a,10,11,11a-Tetrahydroxy-9,15a-dimethyl-1-(5-oxo-2,5-dihydrofuran-3-yl)icosahydro-7aH,13aH-cyclopenta[7,8]phenanthro[2,3-b]pyrano[3,2-e][1,4]dioxine-13a-carbaldehyde

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0
Polarare Oberfläche (TPSA)
152 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
10
Frei drehbare Bindungen
2
Schwere Atome
39
Formalladung
0
Komplexität
1.090

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Plant Toxins

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Gefahrenhinweise

Hazards Summary · 1 Eintrag

Emergency treatment: Plants- cardiac glycosides; [HSDB] Intravenous LD50 (cat) = 112 ug/kg; [RTECS] In animals poisoned by milkweed, causes muscular weakness, respiratory paralysis, intestinal stasis, and coma; Pathological evidence that it damages the liver, heart, kidneys, lungs, brain, and intestines; [HSDB] Milkweed (Asclepias spp) contains cardiac glycosides; [Olson, p. 385] Milkweed (Asclepias spp) contains cardenolides that are cardiac toxins; [Goldfrank, p. 1538] See Calotropin.

Toxikologische Informationen

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Natural Pollution Sources · 1 Eintrag

CALOTROPIS PROCERA, A SHRUB NATIVE TO AFRICA, WAS THE FIRST SOURCE FOR ISOLATION OF THE CYCLIC BRIDGED GLYCOSIDES. FROM CALOTROPIS LATEX...WERE SEPARATED CALOTROPIN, CALACTIN, CALOTOXIN, USCHARIDIN, USCHARIN AND VORUSCHARIN -A NEW SERIES OF CARDENOLIDES WITH A COMMON GENIN, CALOTROPAGENIN.

Non-Human Toxicity Excerpts · 5 Einträge

MILKWEED POISONING IN...CATTLE REMAINS A PROBLEM TO RANCHERS, PARTICULARLY WHEN ADEQUATE QUANTITIES OF POTABLE FORAGE ARE UNAVAILABLE OR WHEN MILKWEEDS ARE INCORPORATED IN CUT FEED. ... NERVOUS & GASTROINTESTINAL SYMPTOMS INCLUDE DEPRESSION AND APATHY, WEAKNESS, LOSS OF MUSCLE CONTROL, FALLING, DILATED PUPILS, RESPIRATORY PARALYSIS, INTESTINAL STASIS AND FERMENTATION, AND OCCASIONALLY, DIARRHEA. SOMETIMES TETANIC SEIZURES ARE SEEN. ...SYMPTOMS MAY BEGIN AS EARLY AS 2 HR AFTER INGESTION OF THE PLANT & MAY CONTINUE FOR HR OR DAYS. A POISONED ANIMAL MAY OR MAY NOT EXPERIENCE A PERIOD OF COMA BEFORE DYING. LESIONS AT DEATH INCLUDE ACUTE CATARRHAL GASTROENTERITIS AND CONGESTION OF THE LUNGS & SOMETIMES OF THE KIDNEYS. /MILKWEED POISONING/

Acute toxicity of C procera was studied in Desert sheep given single or multiple doses (6.0 to 0.001 ml/kg) of the latex by oral route, it caused death. The animals developed nervous signs, urination, tachycardia, dyspnea and loss of condition. Severe pathological changes were seen in the liver, kidneys, heart, lungs, brain & intestines, correlated with metabolic changes in the serum. The concn of total lipids in the liver, heart and kidneys was increased.

Chemie und Industrie

Verwendung und Herstellung

UsesA toxin found in Calotropis procera (milkweed); Toxic to cattle and other animals that feed on milkweed; Sequestered by monarch butterflies and used in defense against predators; [HSDB]
General Manufacturing Information · 3 Einträge

CALOTOXIN CONCENTRATIONS IN CALOTROPIS PROCERA WERE MEASURED TO EVALUATE EXTRACT TECHNIQUES & DETERMINE THE LEVELS IN DIFFERENT PLANT COMPONENTS. CONCN FROM UNEXTRACTED COMPONENTS: WHOLE PLANT 190 UG/G; STEMS 184 UG/G; LEAVES 92 UG/G; PODS 0 UG/G. CONCN FROM HEXANE EXTRACTION: WHOLE PLANT 225 UG/G; STEMS 188 UG/G; LEAVES 195 UG/G; PODS 176 UG/G. TRACE AMOUNTS WERE NOT DETECTED IN PLANT COMPONENTS FROM HEXANE AND METHANOL EXTRACTION. THE PRESUMPTIVE NUTRIENT VALUE OF EXTRACTED RESIDUE FROM CALOTROPIS PROCERA SUPPORTS CULTIVATION OF THIS PLANT SPECIES AS A POTENTIAL FUEL AND FEED RESOURCE.

THE POTENT BIOLOGICAL ACTIVITY OF MILKWEED-DERIVED CARDENOLIDES IS MANIFESTED IN ANIMALS THAT FEED DIRECTLY ON MILKWEEDS, AND IN THOSE THAT PREY ON MILKWEED FEEDERS. /CARDENOLIDES/

...OF PARTICULAR INTEREST ARE INSECTS THAT ARE NOT ONLY TOLERANT OF THE /MILKWEED/ POISONS, BUT ADDITIONALLY HAVE THE CAPABILITY TO SEQUESTER THEM FROM THEIR PLANT HOST AND STORE THEM FOR DEFENSE AGAINST THEIR PREDATORS. ... THE MOST THOROUGHLY STUDIED WITH...MILKWEEDS /ARE/ MONARCH BUTTERFLIES, WHICH FEED UPON ASCLEPIAS DURING LARVAL DEVELOPMENT; AND BLUEJAYS, EXPERIMENTAL PREDATORS OF MONARCHS. /CARDENOLIDES/

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Datenbank-Bezeichner

CAS
20304-49-8
PubChem CID
56840852
DTXSID
DTXSID40174193

Acute toxicity of C procera was studied in Desert sheep given single or multiple doses (6.0 to 0.001 ml/kg) of the latex by iv route, it caused death in both species. The animals developed nervous signs, urination, tachycardia, dyspnea and loss of condition. Severe pathological changes were seen in the liver, kidneys, heart, lungs, brain & intestines, correlated with metabolic changes in the serum. The concn of total lipids in the liver, heart and kidneys was increased.

Acute toxicity of C procera was studied in Desert sheep given single or multiple doses (6.0 to 0.001 ml/kg) of the latex by ip route, it caused death. The animals developed nervous signs, urination, tachycardia, dyspnea and loss of condition. Severe pathological changes were seen in the liver, kidneys, heart, lungs, brain & intestines, correlated with metabolic changes in the serum. The concn of total lipids in the liver, heart and kidneys was increased.

For more Non-Human Toxicity Excerpts (Complete) data for CALOTOXIN (9 total), please visit the HSDB record page.