Gelsedine (CHEM003060)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:08:50 UTC
Update Date2026-05-21 01:36:18 UTC
Accession NumberCHEM003060
Identification
Common NameGelsedine
ClassSmall Molecule
DescriptionGelsedine is an indole alkaloid found in the plant species Gelsemium (Loganiaceae). It has a rich background in Chinese medicine, yet specific biological roles of the compound are poorly documented (1).
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ether
  • Natural Compound
  • Organic Compound
  • PFAS
  • Phytotoxin
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC19H24N2O3
Average Molecular Mass328.406 g/mol
Monoisotopic Mass328.179 g/mol
CAS Registry Number7096-96-0
IUPAC NameNot Available
Traditional Name(1'R,3S,4'S,6'R,7'R,8'S)-6'-ethyl-1-methoxy-10'-oxa-5'-azaspiro[indole-3,2'-tricyclo[5.3.1.0⁴,⁸]undecane]-2-one
SMILES[H][C@]1(CC)N[C@@]2([H])C[C@@]3(C(=O)N(OC)C4=CC=CC=C34)[C@@]3([H])C[C@]1([H])[C@]2([H])CO3
InChI IdentifierInChI=1S/C19H24N2O3/c1-3-14-11-8-17-19(9-15(20-14)12(11)10-24-17)13-6-4-5-7-16(13)21(23-2)18(19)22/h4-7,11-12,14-15,17,20H,3,8-10H2,1-2H3/t11-,12+,14-,15+,17-,19+/m1/s1
InChI KeyLDBVYQSHIPCQPT-CTSQFDBHSA-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
  • Oxepane
  • Aralkylamine
  • Oxane
  • Benzenoid
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Dialkyl ether
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.22 g/LALOGPS
logP1.87ALOGPS
logP1.73ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)11.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.8 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.22 m³·mol⁻¹ChemAxon
Polarizability35.44 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, Positivesplash10-004i-0009000000-8d7c415f5f5e87d3a7c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004s-1095000000-918627db64b6cb5c2766Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9020000000-41790aabc16c1c09d898Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0029000000-c783650cc8e1e5d93e06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-4094000000-9d1de570efbce8e1e2a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9110000000-95c0c2ad408b4e620ee4Spectrum
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/SourcesGelsedine is an indole alkaloid found in the plant species Gelsemium (Loganiaceae).
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 IDC00025088
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID21589070
Kegg Compound IDC19982
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available