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Record Information
Version2.0
Creation Date2009-07-23 18:26:16 UTC
Update Date2014-12-24 20:25:58 UTC
Accession NumberT3D3099
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)
Compound Type
  • Amine
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
C-toxiferin I
C-toxiferine I
Toxiferine I
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 KeyInChIKey=UAMHUVZCGJSLHZ-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
LogPNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00li-0000009000-e0eabdf159c15b1f67d6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0000009000-b88c46115daae7b91827JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-0075097000-7cab0ac67fee4ab45812JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000009000-c69b11a5b5f25e7fd453JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f8i-0000009000-d295f63e0e02413e5c62JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-0009005000-59307358fe90fbd0395fJSpectraViewer
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)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID5281411
ChEMBL IDCHEMBL231047
ChemSpider ID23288958
KEGG IDC09246
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDToxiferine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkToxiferine
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA1
Uniprot ID:
P02708
Molecular Weight:
54545.235 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNB1
Uniprot ID:
P11230
Molecular Weight:
56697.9 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Acetylcholine-activated cation-selective channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRND
Uniprot ID:
Q07001
Molecular Weight:
58894.55 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Cation transmembrane transporter activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNE
Uniprot ID:
Q04844
Molecular Weight:
54696.54 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNG
Uniprot ID:
P07510
Molecular Weight:
57882.8 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Receptor binding
Specific Function:
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma.
Gene Name:
CHRNA10
Uniprot ID:
Q9GZZ6
Molecular Weight:
49704.295 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Drug binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular Weight:
59764.82 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA3
Uniprot ID:
P32297
Molecular Weight:
57479.54 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodium ions.
Gene Name:
CHRNA4
Uniprot ID:
P43681
Molecular Weight:
69956.47 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA5
Uniprot ID:
P30532
Molecular Weight:
53053.965 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Acetylcholine-activated cation-selective channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA6
Uniprot ID:
Q15825
Molecular Weight:
56897.745 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Toxic substance binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is blocked by alpha-bungarotoxin.
Gene Name:
CHRNA7
Uniprot ID:
P36544
Molecular Weight:
56448.925 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Calcium channel activity
Specific Function:
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding induces a conformation change that leads to the opening of an ion-conducting channel across the plasma membrane (PubMed:11752216, PubMed:25282151). The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane (PubMed:11752216, PubMed:25282151). In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma. May also regulate keratinocyte adhesion (PubMed:11021840).
Gene Name:
CHRNA9
Uniprot ID:
Q9UGM1
Molecular Weight:
54806.63 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodiun ions.
Gene Name:
CHRNB2
Uniprot ID:
P17787
Molecular Weight:
57018.575 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Drug binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNB3
Uniprot ID:
Q05901
Molecular Weight:
52728.215 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNB4
Uniprot ID:
P30926
Molecular Weight:
56378.985 Da
References
  1. Wikipedia. Curare. Last Updated 9 June 2009. [Link]