Alcuronium (CHEM002433)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (17)XML
Record Information
Version1.0
Creation Date2009-07-23 18:26:15 UTC
Update Date2016-11-09 01:08:46 UTC
Accession NumberCHEM002433
Identification
Common NameAlcuronium
ClassSmall Molecule
DescriptionAlcuronium is a type of curare, a plant toxin known for its use as paralyzing arrow poison by South American indigenous people. It can be extracted from a variety of plants, including Strychnos toxifera and Chondrodendron tomentosum. Curares are active only by an injection. They are harmless if taken orally because curare compounds are too large and too highly charged to pass through the lining of the digestive tract to be absorbed into the blood. (1)
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Bromide Compound
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC44H50Br2N4O2
Average Molecular Mass826.701 g/mol
Monoisotopic Mass824.230 g/mol
CAS Registry Number23214-96-2
IUPAC Name(1S,9Z,11S,13S,25Z,27S,28E,33S,35S,37E,38S)-28,37-bis(2-hydroxyethylidene)-14,30-bis(prop-2-en-1-yl)-8,14,24,30-tetraazaundecacyclo[25.5.2.2¹¹,¹⁴.1¹,⁸.1¹⁰,¹⁷.0²,⁷.0¹³,¹⁷.0¹⁸,²³.0³⁰,³³.0²⁴,³⁵.0²⁶,³⁸]octatriaconta-2,4,6,9,18,20,22,25-octaene-14,30-diium dibromide
Traditional Name(1S,9Z,11S,13S,25Z,27S,28E,33S,35S,37E,38S)-28,37-bis(2-hydroxyethylidene)-14,30-bis(prop-2-en-1-yl)-8,14,24,30-tetraazaundecacyclo[25.5.2.2¹¹,¹⁴.1¹,⁸.1¹⁰,¹⁷.0²,⁷.0¹³,¹⁷.0¹⁸,²³.0³⁰,³³.0²⁴,³⁵.0²⁶,³⁸]octatriaconta-2,4,6,9,18,20,22,25-octaene-14,30-diium dibromide
SMILES[Br-].[Br-].[H]\C(CO)=C1/C[N+]2(CC=C)CCC34C5=CC=CC=C5N5\C([H])=C6/[C@]7([H])N(\C([H])=C(/[C@@]35[H])[C@@]1([H])C[C@]24[H])C1=CC=CC=C1[C@@]71CC[N+]2(CC=C)C\C(=C(/[H])CO)[C@]6([H])C[C@@]12[H]
InChI IdentifierInChI=1S/C44H50N4O2.2BrH/c1-3-17-47-19-15-43-35-9-5-7-11-37(35)45-26-34-32-24-40-44(16-20-48(40,18-4-2)28-30(32)14-22-50)36-10-6-8-12-38(36)46(42(34)44)25-33(41(43)45)31(23-39(43)47)29(27-47)13-21-49;;/h3-14,25-26,31-32,39-42,49-50H,1-2,15-24,27-28H2;2*1H/q+2;;/p-2/b29-13-,30-14-,33-25-,34-26-;;/t31-,32-,39-,40-,41-,42-,43+,44?,47?,48?;;/m0../s1
InChI KeyBXTUHNWXQLWICJ-FRBQZQGESA-L
Chemical Taxonomy
Description belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassStrychnos alkaloids
Sub ClassNot Available
Direct ParentStrychnos alkaloids
Alternative Parents
Substituents
  • Strychnan skeleton
  • Akuammicine-skeleton
  • Stemmadenine-skeleton
  • Curan skeleton
  • Carbazole
  • Indolizidine
  • Indole or derivatives
  • Tertiary aliphatic/aromatic amine
  • Aralkylamine
  • Benzenoid
  • N-alkylpyrrolidine
  • Piperidine
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Pyrrolidine
  • Tertiary amine
  • Allylamine
  • Azacycle
  • Organoheterocyclic compound
  • Enamine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic bromide salt
  • Organic salt
  • Organic zwitterion
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
PenicillinsNot AvailableNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00064 g/LALOGPS
logP2.46ALOGPS
logP-4.3ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)15.3ChemAxon
pKa (Strongest Basic)1.52ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.94 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity226.64 m³·mol⁻¹ChemAxon
Polarizability77.42 ųChemAxon
Number of Rings11ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-056r-0000000960-a765e2854a5dc0c3c867Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-2200002910-dfdcbb90dc1ed8d6dfc2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9103006500-b07e16c1b4a526e281afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000390-604df025185c01223197Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-0000000940-e944f542ba924455b9b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-1302110900-f665118bbce154c62962Spectrum
Toxicity Profile
Route of ExposureInjection (sting/bite) (1)
Mechanism of ToxicityCurare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAlcuronium is a type of curare, a plant toxin known for its use as paralyzing arrow poison by South American indigenous people. It can be extracted from a variety of plants, including Strychnos toxifera and Chondrodendron tomentosum. (1)
Minimum Risk LevelNot Available
Health EffectsCurare is a muscle relaxant that can lead to death from asphyxiation, as the respiratory muscles are unable to contract. (1)
SymptomsCurare is a muscle relaxant and thus causes paraylsis. (1)
TreatmentThe antidote for curare poisoning is an acetylcholinesterase inhibitor (anti-cholinesterase), such as physostigmine or neostigmine. (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 LinkAlcuronium chloride
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID44427887
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available