Toxiferine (CHEM002434)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (16)XML
Record Information
Version1.0
Creation Date2009-07-23 18:26:16 UTC
Update Date2016-11-09 01:08:46 UTC
Accession NumberCHEM002434
Identification
Common NameToxiferine
ClassSmall Molecule
DescriptionToxiferine 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
  • T3DB toxins
Contaminant Type
  • Amine
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC40H46Cl2N4O2
Average Molecular Mass685.725 g/mol
Monoisotopic Mass684.300 g/mol
CAS Registry Number6888-23-9
IUPAC Name(1S,9Z,11S,13S,25Z,27S,28E,33S,35S,37E,38S)-28,37-bis(2-hydroxyethylidene)-14,30-dimethyl-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 dichloride
Traditional Name(1S,9Z,11S,13S,25Z,27S,28E,33S,35S,37E,38S)-28,37-bis(2-hydroxyethylidene)-14,30-dimethyl-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 dichloride
SMILES[Cl-].[Cl-].[H]\C(CO)=C1/C[N+]2(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(C)C\C(=C(/[H])CO)[C@]6([H])C[C@@]12[H]
InChI IdentifierInChI=1S/C40H46N4O2.2ClH/c1-43-15-13-39-31-7-3-5-9-33(31)41-22-30-28-20-36-40(14-16-44(36,2)24-26(28)12-18-46)32-8-4-6-10-34(32)42(38(30)40)21-29(37(39)41)27(19-35(39)43)25(23-43)11-17-45;;/h3-12,21-22,27-28,35-38,45-46H,13-20,23-24H2,1-2H3;2*1H/q+2;;/p-2/b25-11-,26-12-,29-21-,30-22-;;/t27-,28-,35-,36-,37-,38-,39+,40?,43?,44?;;/m0../s1
InChI KeyUAMHUVZCGJSLHZ-ICRMOYGQSA-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 chloride 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
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Salivary secretionNot Availablemap04970
ApplicationsNot Available
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 Solubility0.0006 g/LALOGPS
logP-0.47ALOGPS
logP-5.7ChemAxon
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 Count2ChemAxon
Refractivity208.32 m³·mol⁻¹ChemAxon
Polarizability70.29 ųChemAxon
Number of Rings11ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00li-0000009000-e0eabdf159c15b1f67d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0000009000-b88c46115daae7b91827Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-0075097000-7cab0ac67fee4ab45812Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000009000-c69b11a5b5f25e7fd453Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f8i-0000009000-d295f63e0e02413e5c62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-0009005000-59307358fe90fbd0395fSpectrum
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/SourcesToxiferine 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 LinkToxiferine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID44427885
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available