Aconitine (CHEM002416)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2009-07-23 18:26:06 UTC
Update Date2016-11-09 01:08:46 UTC
Accession NumberCHEM002416
Identification
Common NameAconitine
ClassSmall Molecule
DescriptionAconitine is a plant toxin found in species of wolfsbane (Aconitum genus). It is a neurotoxin previously used as an antipyretic and analgesic, and still has some limited application in herbal medicine. (1). The toxic effects of Aconitine have been tested in a variety of different test animals, including mammals (dog, cat, guinea pig, mouse, rat and rabbit), frogs and pigeons. Depending on the route of exposure, the observed toxic effects were: local anesthetic effect, diarrhea, convulsions, arrhythmias or death. According to a review of different reports of aconite poisoning in humans the following clinical features were observed: Neurological, Cardiovascular, Ventricular arrhythmias, Gastrointestinal.
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC34H47NO11
Average Molecular Mass645.737 g/mol
Monoisotopic Mass645.315 g/mol
CAS Registry Number302-27-2
IUPAC Name(1S,2R,3R,4R,5R,6S,7S,8R,9R,13R,14R,16S,17S,18R)-8-(acetyloxy)-11-ethyl-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate
Traditional Nameaconitine
SMILES[H][C@@]12C[C@@]3(O)[C@]([H])(OC(=O)C4=CC=CC=C4)[C@]1([H])[C@@](OC(C)=O)([C@@]1([H])[C@]([H])(OC)[C@@]4([H])[C@]22C1([H])N(CC)C[C@]4(COC)[C@]([H])(O)C[C@]2([H])OC)[C@@]([H])(O)[C@]3([H])OC
InChI IdentifierInChI=1S/C34H47NO11/c1-7-35-15-31(16-41-3)20(37)13-21(42-4)33-19-14-32(40)28(45-30(39)18-11-9-8-10-12-18)22(19)34(46-17(2)36,27(38)29(32)44-6)23(26(33)35)24(43-5)25(31)33/h8-12,19-29,37-38,40H,7,13-16H2,1-6H3/t19-,20?,21+,22-,23+,24+,25-,26?,27+,28-,29+,31+,32-,33+,34-/m1/s1
InChI KeyXFSBVAOIAHNAPC-BHMXGGQCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAconitane-type diterpenoid alkaloids
Alternative Parents
Substituents
  • Aconitane-type diterpenoid alkaloid
  • Quinolidine
  • Benzoate ester
  • Alkaloid or derivatives
  • Benzoic acid or derivatives
  • Benzoyl
  • Azepane
  • Benzenoid
  • Piperidine
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Tertiary alcohol
  • Cyclic alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell junction
  • Cytoplasm
  • Extracellular
  • Microsome
  • Mitochondrion
  • Nerve Fiber
  • Plasma Membrane
  • Sarcoplasmic Reticulum
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Bacterial ChemotaxisNot AvailableNot Available
Antiarrhythmic DrugsNot AvailableNot Available
Rna polymeraseNot Availablemap03020
AnticonvulsantsNot AvailableNot Available
ApoptosisNot Availablemap04210
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point204°C
Boiling PointNot Available
Solubility0.31 mg/mL at 25°C [SEIDELL,A (1941)]
Predicted Properties
PropertyValueSource
Water Solubility0.71 g/LALOGPS
logP1.68ALOGPS
logP-0.54ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.53ChemAxon
pKa (Strongest Basic)9.74ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area153.45 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity161.8 m³·mol⁻¹ChemAxon
Polarizability67.75 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-054k-0200069000-d5c43adf2d9e5a964f8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1400095000-f69fe66a37b8742f9d88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900330000-f75578a0c542f4c59099Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3100039000-2583a09e7f0123c13d6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-4200096000-b0486e36508050714f60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i0-9400050000-88bb6a79c21e8a17f798Spectrum
Toxicity Profile
Route of ExposureOral (ingestion) (2) ; dermal (2)
Mechanism of ToxicityAconitine opens voltage-gated sodium channed in the heart and other tissues. (1)
MetabolismNot Available
Toxicity ValuesLD50: 0.166 mg/kg (Intravenous, Mouse) (1) LD50: 0.328 mg/kg (Intraperitoneal, Mouse) (1) LD50: 1 mg/kg (Oral, Mouse) (1)
Lethal Dose1.5 to 6 mg for an adult human. (1)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAconitine is a plant toxin found in species of wolfsbane (Aconitum genus). It is a neurotoxin previously used as an antipyretic and analgesic, and still has some limited application in herbal medicine. (1)
Minimum Risk LevelNot Available
Health EffectsAconitine may cause death from respiratory paralysis and cardiac arrest. (1)
SymptomsSymptoms of acontine poisoning include paresthesia of the whole body, starting from the extremities, anesthesia, sweating and cooling of the body, nausea, and vomiting. Sometimes there is strong pain, accompanied by cramps, or diarrhea. (1)
TreatmentAs there is no antidote to acontine, treatment is symptomatic and may include administering atropine, strychnine or barakol. (1)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAconitine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available