ContaminantDB: Anisatin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (44)XML

Record Information

Version

1.0

Creation Date

2009-07-23 18:26:04 UTC

Update Date

2026-04-05 15:25:32 UTC

Accession Number

CHEM002412

Identification

Common Name

Anisatin

Class

Small Molecule

Description

Anisatin is an exogenous compound with the formula C15H20O8 and an average molecular weight of 328.31 g/mol. It exists as a solid at room temperature. Anisatin belongs to the terpene lactones, a subclass of prenol lipids within the organic compounds. The compound acts as a GABA system antagonist and has 19 recorded protein targets, including Gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1), Gamma-aminobutyric acid receptor subunit alpha-2 (GABRA2), Gamma-aminobutyric acid receptor subunit alpha-3 (GABRA3), and Gamma-aminobutyric acid receptor subunit alpha-4 (GABRA4), among 15 other proteins. Anisatin binds non-competitively to the picrotoxinin site of the GABA receptor, which reduces the probability of the receptor channel opening and prolongs its closed time.

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Ester
Ether
Food Toxin
Human Neurotoxin
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Anisatin, 1S-(1alpha,4beta,5beta,6beta,7beta,9alpha,9abeta)-isomer	MeSH
Shikimin	MeSH

Chemical Formula

C₁₅H₂₀O₈

Average Molecular Mass

328.315 g/mol

Monoisotopic Mass

328.116 g/mol

CAS Registry Number

5230-87-5

IUPAC Name

Not Available

Traditional Name

4',5',7',11'-tetrahydroxy-2',7'-dimethyl-9'-oxaspiro[oxetane-3,6'-tricyclo[6.3.1.0¹,⁵]dodecane]-4,10'-dione

SMILES

CC1CC(O)C2(O)C3(COC3=O)C(C)(O)C3CC12C(O)C(=O)O3

InChI Identifier

InChI=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 Key

GEVWHIDSUOMVRI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene 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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	78.5 g/L	ALOGPS
logP	-0.89	ALOGPS
logP	-2.1	ChemAxon
logS	-0.62	ALOGPS
pKa (Strongest Acidic)	12.01	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.91 m³·mol⁻¹	ChemAxon
Polarizability	30.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0089000000-d47fe4e58a9ffc9fd6ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fr-1097000000-a56f69138a9be5e87f43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00or-2190000000-445fb0489121c0781dd7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0092000000-b1bf49a2d97acde953d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-0095000000-8d08cabc3669333d8059	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-5090000000-732d45551eeae6456c94	Spectrum

Toxicity Profile

Route of Exposure

Oral (ingestion) (3) ; dermal (3)

Mechanism of Toxicity

Anisatin 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)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Anisatin 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 Level

Not Available

Health Effects

Death may result from respiratory paralysis. (2)

Symptoms

Symptoms of anisatin poisoning include diarrhea, vomiting, and stomach pain, followed by nervous system excitation, seizures, loss of consciousness. (2)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Anisatin

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

171029

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Anisatin (CHEM002412)

Structure for CHEM002412: Anisatin