Anisatin (CHEM002412)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (19)XML
Record Information
Version1.0
Creation Date2009-07-23 18:26:04 UTC
Update Date2026-04-05 15:25:32 UTC
Accession NumberCHEM002412
Identification
Common NameAnisatin
ClassSmall Molecule
DescriptionAnisatin is a plant toxin found in the Japanese star anise (Illicium anisatum). The Japanese star anise has been burned as incense in Japan, where it is known as shikimi, as well as used in topical folk remedies. (2)
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Ester
  • Ether
  • Food Toxin
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Anisatin, 1S-(1alpha,4beta,5beta,6beta,7beta,9alpha,9abeta)-isomerMeSH
ShikiminMeSH
Chemical FormulaC15H20O8
Average Molecular Mass328.315 g/mol
Monoisotopic Mass328.116 g/mol
CAS Registry Number5230-87-5
IUPAC Name4',5',7',11'-tetrahydroxy-2',7'-dimethyl-9'-oxaspiro[oxetane-3,6'-tricyclo[6.3.1.0¹,⁵]dodecane]-4,10'-dione
Traditional Name4',5',7',11'-tetrahydroxy-2',7'-dimethyl-9'-oxaspiro[oxetane-3,6'-tricyclo[6.3.1.0¹,⁵]dodecane]-4,10'-dione
SMILESCC1CC(O)C2(O)C3(COC3=O)C(C)(O)C3CC12C(O)C(=O)O3
InChI IdentifierInChI=1S/C15H20O8/c1-6-3-7(16)15(21)13(6)4-8(23-10(18)9(13)17)12(2,20)14(15)5-22-11(14)19/h6-9,16-17,20-21H,3-5H2,1-2H3
InChI KeyGEVWHIDSUOMVRI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Sesquiterpenoid
  • Prezizaane sesquiterpenoid
  • Delta valerolactone
  • Delta_valerolactone
  • Dicarboxylic acid or derivatives
  • Oxane
  • Tertiary alcohol
  • Beta_propiolactone
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxetane
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • 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 Solubility78.5 g/LALOGPS
logP-0.89ALOGPS
logP-2.1ChemAxon
logS-0.62ALOGPS
pKa (Strongest Acidic)12.01ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.91 m³·mol⁻¹ChemAxon
Polarizability30.21 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0089000000-d47fe4e58a9ffc9fd6abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-1097000000-a56f69138a9be5e87f43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-2190000000-445fb0489121c0781dd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0092000000-b1bf49a2d97acde953d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-0095000000-8d08cabc3669333d8059Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-5090000000-732d45551eeae6456c94Spectrum
Toxicity Profile
Route of ExposureOral (ingestion) (3) ; dermal (3)
Mechanism of ToxicityAnisatin acts as a GABA system antagonist. It binds non-competitively to the picrotoxinin site of the GABA receptor, prolonging the closed time of the receptor channel and reducing the probability of it opening. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAnisatin is a plant toxin found in the Japanese star anise (Illicium anisatum). The Japanese star anise has been burned as incense in Japan, where it is known as shikimi, as well as used in topical folk remedies. (2)
Minimum Risk LevelNot Available
Health EffectsDeath may result from respiratory paralysis. (2)
SymptomsSymptoms of anisatin poisoning include diarrhea, vomiting, and stomach pain, followed by nervous system excitation, seizures, loss of consciousness. (2)
TreatmentNot Available
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 LinkAnisatin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID171029
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available