Gelsemine (T3D4071)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 05:02:45 UTC
Update Date2014-12-24 20:26:37 UTC
Accession NumberT3D4071
Identification
Common NameGelsemine
ClassSmall Molecule
DescriptionGelsemine is a toxic alkaloid found in the plant Gelsemium sempervirens. It has convulsant effects with a similar mechanism of action to strychnine. Due to its complex structure, gelsemine has been the target for a number of total synthesis projects.
Compound Type
  • Amine
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC20H22N2O2
Average Molecular Mass322.401 g/mol
Monoisotopic Mass322.168 g/mol
CAS Registry Number509-15-9
IUPAC Name(2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecane]-2-ol
Traditional Name(2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecane]-2-ol
SMILES[H][C@]12CO[C@]3([H])CC1([H])[C@@]1(CN(C)[C@@]2([H])[C@]1([H])[C@@]31C(O)=NC2=CC=CC=C12)C=C
InChI IdentifierInChI=1S/C20H22N2O2/c1-3-19-10-22(2)16-11-9-24-15(8-13(11)19)20(17(16)19)12-6-4-5-7-14(12)21-18(20)23/h3-7,11,13,15-17H,1,8-10H2,2H3,(H,21,23)/t11-,13?,15+,16+,17-,19-,20-/m0/s1
InChI KeyInChIKey=NFYYATWFXNPTRM-ICFOCEFXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassGelsemium alkaloids
Sub ClassNot Available
Direct ParentGelsemium alkaloids
Alternative Parents
Substituents
  • Gelsemium skeleton
  • Indole or derivatives
  • Dihydroindole
  • Isoindoline
  • Isoindole or derivatives
  • Oxepane
  • Aralkylamine
  • Oxane
  • Piperidine
  • N-alkylpyrrolidine
  • Benzenoid
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
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 Solubility0.088 g/LALOGPS
logP1.49ALOGPS
logP-0.59ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.88ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.52 m³·mol⁻¹ChemAxon
Polarizability34.65 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0019000000-2d59eb57ec3278195ff12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0259000000-5bdc5c9f0ec7425334342016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-8920000000-ff7118dd6e7438a2adf62016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-3a4e2cd4e51f802847342016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-3019000000-f600237c1ff6849cd3012016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9230000000-c3c63118a4dbe45710052016-08-03View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityGelsemine has convulsant effects with a similar mechanism of action to strychnine. Strychnine is a neurotoxin which acts as an antagonist of glycine and acetylcholine receptors. It primarily affects the motor nerves in the spinal cord which control muscle contraction. An impulse is triggered at one end of a nerve by the binding of neurotransmitters to the receptors. In the presence of a neuroinhibitor, such as glycine, a greater quantity of excitatory neurotransmitters must bind to receptors before there will be an action potential generated. Glycine acts primarily as an agonist of the glycine receptor, which is a ligand-gated chloride channel in neurons located in the spinal cord and in the brain. This chloride channel will allow the negatively charged chloride ions into the neuron, causing a hyperpolarization which pushes the membrane potential further from threshold. Strychnine is an antagonist of glycine, which means it binds to the same receptor, preventing the inhibitory effects of glycine on the postsynaptic neuron. Therefore, action potentials are triggered with lower levels of excitatory neurotransmitters. When the inhibitory signals are prevented, the motor neurons do will be more easliy activated and the victim will have spastic muscle contractions. Structure of strychnine in complex with ACh binding protein (AChBP). Strychnine is also an antagonist for acetylcholine receptors, which is known to be homologous to the glycine receptor. (Wikipedia)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesGelsemine is a toxic alkaloid found in the plant Gelsemium sempervirens.
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 ID5462429
ChEMBL IDNot Available
ChemSpider ID4575404
KEGG IDC09207
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
MSDST3D4071.pdf
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available