Azaspiracid (CHEM002117)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2009-07-15 20:45:52 UTC
Update Date2026-03-31 17:39:10 UTC
Accession NumberCHEM002117
Identification
Common NameAzaspiracid
ClassSmall Molecule
DescriptionAzaspiracid is found in mollusks. Azaspiracid is an alkaloid from Mytilus edulis (blue mussel). Shellfish toxin.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Ether
  • Food Toxin
  • Marine Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Azaspiracid-1MeSH
Chemical FormulaC47H71NO12
Average Molecular Mass842.066 g/mol
Monoisotopic Mass841.498 g/mol
CAS Registry Number214899-21-5
IUPAC Name(4E)-5-[(2R,3aS,5R,5'R,6S,6''S,7aS)-2-[(S)-hydroxy[(2R,3R,5S,6S)-2-hydroxy-3,5-dimethyl-6-{3-[(1'S,2R,2'S,3R,5S,6'S,8'R,10'R)-3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0²,⁶]dodecane]-8'-yl]prop-1-en-2-yl}oxan-2-yl]methyl]-6-methyl-2,3,3a,5'',6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl]pent-4-enoic acid
Traditional Name(4E)-5-[(2R,3aS,5R,5'R,6S,6''S,7aS)-2-[(S)-hydroxy[(2R,3R,5S,6S)-2-hydroxy-3,5-dimethyl-6-{3-[(1'S,2R,2'S,3R,5S,6'S,8'R,10'R)-3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0²,⁶]dodecane]-8'-yl]prop-1-en-2-yl}oxan-2-yl]methyl]-6-methyl-2,3,3a,5'',6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl]pent-4-enoic acid
SMILES[H]\C(CCC(O)=O)=C(\[H])[C@]1([H])CC=C[C@]2(CC[C@]3(O2)O[C@@]2([H])C[C@@]([H])(O[C@@]2([H])C[C@]3([H])C)[C@]([H])(O)[C@]2(O)O[C@]([H])(C(=C)C[C@]34C[C@]([H])(C)C[C@]([H])(O3)[C@]3([H])O[C@@]5(C[C@]3([H])O4)NC[C@@]([H])(C)C[C@@]5([H])C)[C@@]([H])(C)C[C@@]2([H])C)O1
InChI IdentifierInChI=1S/C47H71NO12/c1-26-18-36-41-38(24-45(58-41)30(5)17-27(2)25-48-45)56-44(22-26,55-36)23-29(4)40-28(3)19-32(7)47(52,59-40)42(51)37-21-35-34(53-37)20-31(6)46(57-35)16-15-43(60-46)14-10-12-33(54-43)11-8-9-13-39(49)50/h8,10-11,14,26-28,30-38,40-42,48,51-52H,4,9,12-13,15-25H2,1-3,5-7H3,(H,49,50)/b11-8+/t26-,27+,28+,30-,31+,32-,33-,34+,35+,36+,37-,38+,40+,41+,42+,43+,44-,45-,46-,47-/m1/s1
InChI KeyAHFHSIVCLPAESC-SJVADWSCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzaspirodecane derivatives
Sub ClassNot Available
Direct ParentAzaspirodecane derivatives
Alternative Parents
Substituents
  • Azaspirodecane
  • Furopyran
  • Medium-chain fatty acid
  • Amino fatty acid
  • Ketal
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Meta-dioxane
  • Monosaccharide
  • Oxane
  • Piperidine
  • Pyran
  • Unsaturated fatty acid
  • Fatty acid
  • Fatty acyl
  • Tetrahydrofuran
  • Furan
  • Secondary alcohol
  • Amino acid or derivatives
  • Hemiacetal
  • Hemiaminal
  • Amino acid
  • Oxacycle
  • Azacycle
  • Secondary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Secondary aliphatic amine
  • Ether
  • Acetal
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Actin Cytoskeleton
  • Actin Filament
  • Cytoskeleton
  • Extracellular
  • Focal adhesion
  • Golgi apparatus
  • Membrane
  • Microtubule
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
EndocytosisNot Availablemap04144
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceColorless amorphorous solid (7).
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
logP3.79ALOGPS
logP4.95ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)3.95ChemAxon
pKa (Strongest Basic)9.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area163.63 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity221.81 m³·mol⁻¹ChemAxon
Polarizability93.43 ųChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ec-0109300030-a602af554f2eefaac6beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2409021000-e565e752e9cd35713891Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-3901000000-9b7dcd2b450c62ab197eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002e-2622982040-7d3136f20dbc01b585baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08ml-0295322340-b5333fa2568e07f2eebeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1910000000-5763e14aa049c6d93e57Spectrum
Toxicity Profile
Route of ExposureOral (2) ; inhalation (2) ; dermal (2) ; eye contact (2)
Mechanism of ToxicityAzaspiracid-4 dose-dependent inhibits the increase in cytosolic Ca2+ levels induced by thapsigargin (Tg) (3). Azaspiracid-2 and Azaspiracid-3 clearly increase cytosolic cAMP levels of human lymphocytes (4).
MetabolismNot Available
Toxicity ValuesLD50: 500-600 mg/kg (Oral, Mouse) (8)
Lethal Dose150 ug/kg for mice. (8)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesExperimentally in cancer research. The toxin is also found in shellfish (2).
Minimum Risk LevelNot Available
Health EffectsPossibly gastroenteritis (1).
SymptomsAbdominal heaviness, vomiting, and profuse watery diarrhea; also nausea, vomiting, and stomach cramps (2, 5).
TreatmentEstablish a patent airway. Anticipate seizures and treat if necessary. For eye contamination, flush eyes immediately with water. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Cover skin burns with dry sterile dressings after decontamination. (9)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAzaspiracid
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID21593892
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available