Gelsemicine (CHEM003030)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (25)XML
Record Information
Version1.0
Creation Date2014-08-29 05:02:33 UTC
Update Date2026-05-21 01:44:43 UTC
Accession NumberCHEM003030
Identification
Common NameGelsemicine
ClassSmall Molecule
DescriptionGelsemicine is a solid organic compound with the chemical formula C20H26N2O4 and an average molecular weight of 358.43 g/mol. Gelsemicine belongs to the gelsemium alkaloids, a class of alkaloids and derivatives within the organic compounds. This exogenous substance is found in or released from 13 recorded sources across several sectors. These sources include electrical and electronic equipment, such as cell phones, capacitors, wires and cables, batteries, and printed circuit boards, as well as one additional source in that sector. It is also associated with synthetic textiles and carpets and rugs within the textiles, leather and furnishings sector, and food packaging within the food, food processing and cookware sector. Additionally, gelsemicine is found in medical devices from the healthcare, pharmaceuticals and veterinary products sector, and lubricants utilized in both the energy, oil and gas sector and the industrial manufacturing and chemical processing sector. One further sector is also recorded as a source. Recorded exposure routes for this compound include inhalation, oral, and touch.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ether
  • Natural Compound
  • Organic Compound
  • PFAS
  • Phytotoxin
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC20H26N2O4
Average Molecular Mass358.431 g/mol
Monoisotopic Mass358.189 g/mol
CAS Registry Number6887-28-1
IUPAC NameNot Available
Traditional Namegelsemicine
SMILES[H][C@]1(CC)N[C@@]2([H])C[C@@]3(C(=O)N(OC)C4=C3C=CC(OC)=C4)[C@@]3([H])C[C@]1([H])[C@]2([H])CO3
InChI IdentifierInChI=1S/C20H26N2O4/c1-4-15-12-8-18-20(9-16(21-15)13(12)10-26-18)14-6-5-11(24-2)7-17(14)22(25-3)19(20)23/h5-7,12-13,15-16,18,21H,4,8-10H2,1-3H3/t12-,13+,15-,16+,18-,20+/m1/s1
InChI KeyRIHQHYIWKHVLRH-XKTBTPLDSA-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
  • C21-norgelsemium skeleton
  • Indole or derivatives
  • Anisole
  • Alkyl aryl ether
  • Oxepane
  • Aralkylamine
  • Oxane
  • Benzenoid
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Dialkyl ether
  • Secondary aliphatic amine
  • Ether
  • Oxacycle
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • 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
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP1.83ALOGPS
logP1.57ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)11.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.03 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.68 m³·mol⁻¹ChemAxon
Polarizability38.62 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-354de36d44da6ed837f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-0019000000-6c458d59dae537e88187Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9321000000-6a51fbd671ec25fa3a74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-15510a5a4de26248c587Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-2019000000-bd63889d2eb020b43503Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9011000000-3d7658ce9e9a3a20af66Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesGelsemicine is an indole alkaloid toxin isolated from Gelsemium Sempervirens, a North American poison plant.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001733
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5462428
Kegg Compound IDC09203
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available