Gymnodimine (CHEM003011)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 04:58:27 UTC
Update Date2016-11-09 01:09:01 UTC
Accession NumberCHEM003011
Identification
Common NameGymnodimine
ClassSmall Molecule
DescriptionGymnodimine is found in mollusks. Gymnodimine is isolated from New Zealand oysters (Tiostrea chilensis) and the dinoflagellate Gymnodinium cf. mikimotoi.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Ester
  • Ether
  • Food Toxin
  • Marine Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC32H45NO4
Average Molecular Mass507.704 g/mol
Monoisotopic Mass507.335 g/mol
CAS Registry Number173792-58-0
IUPAC Name5-[(2E)-19-hydroxy-2,15,18,24-tetramethyl-25-oxa-7-azatetracyclo[20.2.1.0⁶,¹¹.0¹¹,¹⁶]pentacosa-2,6,14,17-tetraen-14-yl]-3-methyl-2,5-dihydrofuran-2-one
Traditional Name5-[(2E)-19-hydroxy-2,15,18,24-tetramethyl-25-oxa-7-azatetracyclo[20.2.1.0⁶,¹¹.0¹¹,¹⁶]pentacosa-2,6,14,17-tetraen-14-yl]-3-methyl-5H-furan-2-one
SMILESCC1CC2CCC(O)C(C)=CC3C(C)=C(CCC33CCCN=C3CC\C=C(C)\C1O2)C1OC(=O)C(C)=C1
InChI IdentifierInChI=1S/C32H45NO4/c1-19-8-6-9-29-32(13-7-15-33-29)14-12-25(28-18-22(4)31(35)37-28)23(5)26(32)17-20(2)27(34)11-10-24-16-21(3)30(19)36-24/h8,17-18,21,24,26-28,30,34H,6-7,9-16H2,1-5H3/b19-8+,20-17+
InChI KeyDVXZVCNEGRKLMW-DCJZOFSYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrahydropyridines. These are derivatives of pyridine in which two double bonds in the pyridine moiety are reduced by adding four hydrogen atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassHydropyridines
Direct ParentTetrahydropyridines
Alternative Parents
Substituents
  • Tetrahydropyridine
  • 2-furanone
  • Dihydrofuran
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Ketimine
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxide
  • Imine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
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 Solubility0.0023 g/LALOGPS
logP5.35ALOGPS
logP5.75ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)14.56ChemAxon
pKa (Strongest Basic)7.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.12 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity150.03 m³·mol⁻¹ChemAxon
Polarizability58.06 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-1000900000-b82637757d6a83477790Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0hb9-5000390000-fee203e839b6cb58df1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0536-0000920000-a3f628705e2e6a0e2a46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00yu-0000900000-9df5c5e06bee3a748b6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-7109700000-10d898778adbd4ed830cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000790000-47d22a5a77d06aeed9a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-2000940000-56e4a3edbcde7f3df501Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-2015900000-843815d7349a6995ca31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0002980000-04328292a60ad2c1c5aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-0000940000-ccbf9796bdaa2ac405d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1004900000-ed2558f11fcccc20e1c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000290000-f29567e802fbf48154c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000910000-9376a4fbf77032e3293aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-5001940000-ee51e656106fa49d7058Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityGymnodimine exerts its toxic effects via binding to nicotinic acetylcholine receptors with picomolar affinities with no sign of apparent reversibility in short time frames. The toxicity of gymnodimine has been attributed, at least in part, to the imine functionality as its reduction leads to a non-toxic derivative. Gymnodimine and 13-desmethyl spirolide C bound to acetylcholine binding proteins. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesGymnodimine is found in mollusks. Gymnodimine is isolated from New Zealand oysters (Tiostrea chilensis) and the dinoflagellate Gymnodinium cf.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0041430
FooDB IDFDB021381
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8611700
ChEBI IDNot Available
PubChem Compound ID10436276
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.