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Calotropin

HCID 16142
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1986-70-5
Standard SMILES
C[C@@H]1C[C@H](O)[C@]2(O)O[C@@H]3C[C@@]4(C=O)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@@H](C6=CC(=O)OC6)CC[C@]54O)C[C@H]3O[C@@H]2O1
InChIKey
OWPWFVVPBYFKBG-NYVHBPEFSA-N
Molecular formula
C29H40O9
Average molar mass
532.6 g/mol
Monoisotopic mass
532.26723285

Overview

Calotropin is a cardenolide glycoside.

Names & identifiers

Preferred name
Calotropin
IUPAC
(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-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

Names & synonyms

CALOTROPINPecilocerin APekilocerin A1986-70-53XK21U1BZS(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-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-carbaldehydeDTXSID10173613NSC-143925(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-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:123041DTXCID4096104(1S,3R,7R,9S,10S,14R,15S,18R,19R,22S)-9,10,22-trihydroxy-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
Show more names
CHEBI:3329HSDB 3470NSC 143925UNII-3XK21U1BZSCALOTROPIN [MI]Card-20(22)-enolide, 14-hydroxy-19-oxo-3,2-((tetrahydro-3,4-dihydroxy-6-methyl-2H-pyran-2,3-diyl)bis(oxy))-, (2alpha(2S,4S,6R),3beta,5alpha)-SCHEMBL868547CHEMBL495949

Properties

Computed structural properties

XLogP
0.9
Topological polar surface area
132 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
9
Rotatable bonds
2
Heavy atoms
38
Formal charge
0
Complexity
1,060

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Plant Toxins
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cardanolides and derivatives [ST0112]
Color/FormRECTANGULAR PLATELETS FROM ALCOHOL OR ETHYL ACETATE
SolubilitySOL IN WATER, ALCOHOL; PRACTICALLY INSOL IN ETHER
Melting Point223 °C WITH DECOMPOSITION
Optical RotationSPECIFIC OPTICAL ROTATION: +66.8 DEG @ 18 °C/D (IN METHANOL); MAX ABSORPTION: 217 NM (LOG E= 4.21); 310 NM (LOG E= 1.49)
Physical DescriptionSolid; Soluble in water; [Merck Index]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Hazards Summary · 1 item

Emergency treatment: Plants- cardiac glycosides; [HSDB] Intraperitoneal LD50 (mouse) = 9800 ug/kg; Causes ataxia, somnolence, and seizures at lethal doses; [RTECS] Milkweed (Asclepias spp) contains cardiac glycosides; [Olson, p. 385] Milkweed (Asclepias spp) contains cardenolides that are cardiac toxins; [Goldfrank, p. 1538] See Calotoxin.

Toxicology

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 item

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 items

MILKWEED POISONING IN SHEEP AND 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/

...(LD50) OF...CALOTROPIN FROM ASCLEPIAS CURASSAVICA (A MILKWEED ALSO KNOWN FOR ITS TOXICITY TO CATTLE), WERE DETERMINED USING MALE SWISS WEBSTER MICE /9.2 MG/KG INTRAPERITONEAL/. ... AFFECTED ANIMALS BECAME QUIET & ATAXIC. RESPIRATION BECAME RAPID BUT LABORED, AND ANIMALS LAID FLAT ON THEIR ABDOMENS WITH THEIR LIMBS SPREAD. THERE WAS SOME TREMBLING, AND SEVERELY AFFECTED ANIMALS CONVULSED. SYMPTOMS APPEARED WITHIN A FEW MINUTES AFTER THE MICE WERE DOSED; AND DEATH, ACCOMPANIED BY CLONIC CONVULSIONS, USUALLY OCCURRED WITHIN 1-2 HR. MICE THAT EXHIBITED SYMPTOMS OF POISONING, BUT SURVIVED, DID NOT APPEAR ILL ON THE DAYS FOLLOWING TREATMENT. NO LESIONS WERE CLEARLY VISIBLE IN MICE THAT DIED WITHIN 24 HR OF BEING DOSED. HEMORRHAGES WERE SEEN IN THE LUNGS OF ANIMALS EUTHANIZED ON THE DAYS FOLLOWING TREATMENT, BUT THE INCIDENCE OF THIS LESION WAS NOT SIGNIFICANTLY GREATER THAN THE INCIDENCE IN THE CONTROL GROUP.

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

(NA+,K+)-ATPASE PRESENT IN CARDIAC MUSCLE HAS BEEN PROPOSED AS THE PHARMACOLOGICAL RECEPTOR FOR CARDIAC GLYCOSIDES. INHIBITION OF THIS ENZYME SYSTEM IS THOUGHT TO BE RESPONSIBLE FOR THE THERAPEUTIC OR TOXIC EFFECTS OF CARDIAC GLYCOSIDES ON THE HEART OF VERTEBRATES. THE ABILITY OF NATURAL AND SEMISYNTHETIC CARDIAC GLYCOSIDES TO INHIBIT (NA+,K+)-ATPASE PREPARATIONS HAS BEEN USED TO PREDICT THE EXTENT OF THEIR EFFECT ON THE MYOCARDIUM. ... THE EVIDENCE CITED...INDICATES THAT ALL CARDENOLIDES MAY BE REGARDED AS HIGHLY TOXIC, THAT SENSITIVITY TO CARDENOLIDES MAY VARY CONSIDERABLY AMONG SPECIES AND THAT THE PRINCIPAL TOXIC EFFECTS ARE ASSOCIATED WITH THE MYOCARDIUM.

Metabolism/Metabolites · 2 items

EARLY STUDIES ON CARDENOLIDE SEQUESTRATION FROM MILKWEEDS WERE CARRIED OUT WITH THE GRASSHOPPER, POEKILOCERUS BUFONIUS. THIS APOSEMATIC NORTH AFRICAN SPECIES, WHICH PROBABLY FEEDS EXCLUSIVELY UPON MILKWEEDS IN NATURE, HAS A POISON GLAND FROM WHICH THE CONTENTS MAY BE EJECTED AS SPRAY DURING THE IMMATURE HOPPER STAGE, OR AS A FOAMY FROTH IN THE ADULT STAGE. THE SECRETION CONTAINS HISTAMINE AND ONE CAT-LETHAL DOSE OF CARDENOLIDE. WHEN REARED ON CALOTROPIS PROCERA OR ASCLEPIAS CURASSAVICA, THE GRASSHOPPERS SECRETION CONTAINED ONLY CALACTIN AND CALOTROPIN IN APPRECIABLE QUANTITIES OF THE SEVEN OR SO RELATED CARDENOLIDES PRESENT IN THE PLANT.

SELECTIVE STORAGE OF SOME CARDENOLIDES FROM AMONG SEVERAL IN THE FOOD PLANT WAS CONFIRMED /IN MONARCH LARVAE/... THAT METABOLIC CONVERSION MIGHT BE INVOLVED IN THIS SELECTIVITY WAS PROVEN BY SEPARATE ADMIN OF GRADED DOSES OF INDIVIDUAL CARDENOLIDES TO MONARCH LARVAE, WITH SUBSEQUENT ANALYSIS OF THE CARDENOLIDE CONTENT OF THE LARVAE & ADULTS. CALACTIN & CALOTROPIN WERE STORED INTACT, BUT USCHARIDIN WAS METABOLIZED TO A MIXTURE OF CALACTIN & CALOTROPIN, WHICH WERE THE CARDENOLIDES STORED. THIS CONVERSION, A REDUCTION, OCCURRED VERY RAPIDLY DURING FEEDING, APPARENTLY IN THE GUT. REASONS OFFERED FOR THE STOREABILITY OF CALACTIN & CALOTROPIN, BUT NOT USCHARIDIN, INCL CHEMICAL INSTABILITY OF THE LATTER IN THE GUT MILIEU, POLARITY (CALACTIN & CALOTROPIN ARE MORE POLAR THAN USCHARIDIN), & THE POSSIBILITY THAT THE C-3'OH IN THE CALACTIN & CALOTROPIN WAS NEEDED FOR BINDING TO A CARRIER AND/OR TISSUE STORAGE SITE.

Uses & manufacturing

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
1986-70-5
PubChem CID
16142
DTXSID
DTXSID10173613
ChEMBL
CHEMBL495949
ChEBI
CHEBI:3329
UNII
3XK21U1BZS
Nikkaji
J7.843C

ROOT EXTRACT FROM CALOTROPIS PROCERA ADMIN ORALLY (20 MG) EVERY OTHER DAY FOR 30 DAYS TO INDIAN DESERT GERBILS (MALES, 30 ANIMALS) RESULTED IN DECR WT OF TESTIS AND EPIDIDYMIS, BODY WT DECR & PYKNOSIS IN TESTICULAR CELLS. TESTICULAR CHROMATIN WAS DESTROYED. LEVELS OF PROTEIN, SIALIC ACID AND RNA IN TESTIS, EPIDIDYMIS AND SEMINAL VESICLES WERE SIGNIFICANTLY REDUCED. ALKALINE PHOSPHATASE ACTIVITY INCR IN TESTIS. SERUM GLUTAMIC PYRUVIC TRANSAMINASE (SGPT) AND GLUTAMIC OXALOACETIC TRANSAMINASE (SGOT) ACTIVITY & CHOLESTEROL LEVELS INCR. HEMATOCRIT AND HEMOGLOBIN VALUES WERE INCR SLIGHTLY & BLOOD SUGAR AND BLOOD UREA LEVELS SIGNIFICANTLY INCR.

When Desert sheep were given single or multiple doses (6.0 to 0.001 ml/kg) of the latex of Calotropis procera orally, 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 CALOTROPIN (11 total), please visit the HSDB record page.

UsesAfrican arrow poison isolated from milk sap of Calotropis procera; [Merck Index]
Methods of Manufacturing · 1 item

AFRICAN ARROW POISON ISOLATED FROM MILK SAP OF CALOTROPIS PROCERA DRYAND, ASCLEPIADACEAE. ISOLATION: LEWIN, ARCH EXP PATH PHARMAKOL 71, 142 (1913); HESSE ET AL; ANN 526, 252 (1936); 566, 130 (1950); RAJAGOPALAN ET AL, HELV CHIM ACTA 38, 1809 (1955).

General Manufacturing Information · 2 items

CALOTROPIN CONCENTRATIONS IN CALOTROPIS PROCERA WERE MEASURED TO EVALUATE EXTRACTION TECHNIQUES & DETERMINE THE LEVELS IN DIFFERENT PLANT COMPONENTS. CONCN FROM UNEXTRACTED COMPONENTS: WHOLE PLANT 569 UG/G; STEMS 734 UG/G; LEAVES 275 UG/G; PODS 313 UG/G. CONCN FROM HEXANE EXTRACTION: WHOLE PLANT 749 UG/G; STEMS 565 UG/G; LEAVES 325 UG/G; PODS 263 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.

...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/