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Mesaconitine (T3D4065)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 05:01:08 UTC
Update Date2014-12-24 20:26:37 UTC
Accession NumberT3D4065
Identification
Common NameMesaconitine
ClassSmall Molecule
DescriptionMesaconitine is one of the Aconitum sp. alkaloids. It stimulates β-adrenoceptors and the consequent activation of intracellular processes can lead to the long-lasting changes in excitability.
Compound Type
  • Amine
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC33H45NO11
Average Molecular Mass631.711 g/mol
Monoisotopic Mass631.299 g/mol
CAS Registry Number2752-64-9
IUPAC Name8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate
Traditional Name8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate
SMILESCOCC12CN(C)C3C4C(OC)C1C3(C1CC3(O)C(OC(=O)C5=CC=CC=C5)C1C4(OC(C)=O)C(O)C3OC)C(CC2O)OC
InChI IdentifierInChI=1/C33H45NO11/c1-16(35)45-33-21-18(13-31(39,28(43-6)26(33)37)27(21)44-29(38)17-10-8-7-9-11-17)32-20(41-4)12-19(36)30(15-40-3)14-34(2)25(32)22(33)23(42-5)24(30)32/h7-11,18-28,36-37,39H,12-15H2,1-6H3
InChI KeyInChIKey=XUHJBXVYNBQQBD-UHFFFAOYNA-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
  • Benzoate ester
  • Quinolidine
  • Benzoic acid or derivatives
  • Alkaloid or derivatives
  • Benzoyl
  • Azepane
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Piperidine
  • Benzenoid
  • Cyclic alcohol
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Secondary alcohol
  • Tertiary amine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Azacycle
  • Dialkyl ether
  • Ether
  • Organopnictogen compound
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondrion
  • Plasma Membrane
  • Soluble Fraction
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Metabolic PathwaysNot AvailableNot Available
ApoptosisNot Availablemap04210
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.9 g/LALOGPS
logP1.37ALOGPS
logP-0.9ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)12.53ChemAxon
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area153.45 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity157.06 m³·mol⁻¹ChemAxon
Polarizability66.01 ųChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0000019000-766a876462aebe7be5eaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0000019000-83a73aa83d2958226219JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0nn9-0200189000-baf6d21a4821ada9cae7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-0400193000-f3bf395297ebd5374820JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900430000-21598a974a53a460cea5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-4200089000-a578bc32eb8578c5fa48JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05gi-4100093000-00f53d6a983a89c374d9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9400160000-da12b8d8d8088e8af9daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000192000-765fd57a6d5f0db4c9f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008c-0000098000-19ca172ff7fe734e2aa8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7o-4200095000-f5aea08b19c931b8481eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2000093000-91892fadee5eaed20390JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000090000-2a3243e73b3c50686587JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-6000090000-5139909e22329238f8b5JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityMesaconitine (MA) is one of the Aconitum sp. alkaloids. The primary toxicity of Aconitum sp. alkaloids is on the heart and the central nervous system. They can induce cardiac flutter or fibrillation, ventricular arrhythmias, and repetitive after-potentials and oscillations following nerve stimulation. The electrophysiological mechanism of the arrhythmogenic effect of aconitine is a delay in the final repolarization phase of the action potential, which initiates premature or triggered excitations. These are due to a removal of inactivation of voltage-dependent Na+ channels. Due to the massive influx of Na+, the excitation is followed by complete inexcitability of nerve cells. Aconitum sp. alkaloids evoke dopamine release from dopaminergic neurons; then excessive extracellular dopamine creates stresses on cellular antioxidant systems and induces neuron apoptosis. They are known cardiotoxins and neurotoxins, and also have embryotoxicity and cytotoxicity. (1) Mesaconitine activates inhibitory noradrenergic neurones of descending inhibitory pathways. Mesaconitine is capable of evoking a long-lasting excitatory action at a low concentration, a depressant action at high concentrations and biphasic effects in an intermediate concentration range, probably via the involvement of the noradrenergic system. The biphasic effect observed during application of 30 and 100 nM mesaconitine is similar to the action of noradrenaline in the rat hippocampal CA1 region. The fact that the two different kinds of actions evoked by 30 and 100 nM mesaconitine in a biphasic manner are selectively prevented by pretreatment with a- and b-adrenoceptor antagonists provides evidence that the effects involve activation of a- and b-receptors. (2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID416228
ChEMBL IDNot Available
ChemSpider ID390349
KEGG IDC08698
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Sun B, Zhang M, Zhang Q, Ma K, Li H, Li F, Dong F, Yan X: Metabonomics study of the effects of pretreatment with glycyrrhetinic acid on mesaconitine-induced toxicity in rats. J Ethnopharmacol. 2014 Jul 3;154(3):839-46. doi: 10.1016/j.jep.2014.05.010. Epub 2014 May 15. [24846827 ]
  2. Ameri A: Effects of the Aconitum alkaloid mesaconitine in rat hippocampal slices and the involvement of alpha- and beta-adrenoceptors. Br J Pharmacol. 1998 Jan;123(2):243-50. [9489612 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available