Anisatin (T3D3074)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (19)XML
Targets (19)
Record Information
Version2.0
Creation Date2009-07-23 18:26:04 UTC
Update Date2014-12-24 20:25:56 UTC
Accession NumberT3D3074
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)
Compound Type
  • Ester
  • Ether
  • Food Toxin
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(-)-anisatin
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 KeyInChIKey=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.
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
LogPNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0089000000-d47fe4e58a9ffc9fd6ab2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-1097000000-a56f69138a9be5e87f432016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-2190000000-445fb0489121c0781dd72016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0092000000-b1bf49a2d97acde953d32016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-0095000000-8d08cabc3669333d80592016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-5090000000-732d45551eeae6456c942016-08-03View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID115121
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC09294
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDAnisatin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkAnisatin
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
  2. Wikipedia. Anisatin. Last Updated 11 March 2009. [Link]
  3. Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Gamma-aminobutyric acid receptor subunit alpha-1
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular Weight:
51801.395 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
2. Gamma-aminobutyric acid receptor subunit alpha-2
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRA2
Uniprot ID:
P47869
Molecular Weight:
51325.85 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
3. Gamma-aminobutyric acid receptor subunit alpha-3
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRA3
Uniprot ID:
P34903
Molecular Weight:
55164.055 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
4. Gamma-aminobutyric acid receptor subunit alpha-4
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRA4
Uniprot ID:
P48169
Molecular Weight:
61622.645 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
5. Gamma-aminobutyric acid receptor subunit alpha-5
General Function:
Transporter activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRA5
Uniprot ID:
P31644
Molecular Weight:
52145.645 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
6. Gamma-aminobutyric acid receptor subunit alpha-6
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRA6
Uniprot ID:
Q16445
Molecular Weight:
51023.69 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
7. Gamma-aminobutyric acid receptor subunit beta-1
General Function:
Ligand-gated ion channel activity
Specific Function:
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Gene Name:
GABRB1
Uniprot ID:
P18505
Molecular Weight:
54234.085 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
8. Gamma-aminobutyric acid receptor subunit beta-2
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
Gene Name:
GABRB2
Uniprot ID:
P47870
Molecular Weight:
59149.895 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
9. Gamma-aminobutyric acid receptor subunit beta-3
General Function:
Gaba-gated chloride ion channel activity
Specific Function:
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
Gene Name:
GABRB3
Uniprot ID:
P28472
Molecular Weight:
54115.04 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
10. Gamma-aminobutyric acid receptor subunit delta
General Function:
Gaba-a receptor activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRD
Uniprot ID:
O14764
Molecular Weight:
50707.835 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
11. Gamma-aminobutyric acid receptor subunit epsilon
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRE
Uniprot ID:
P78334
Molecular Weight:
57971.175 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
12. Gamma-aminobutyric acid receptor subunit gamma-1
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRG1
Uniprot ID:
Q8N1C3
Molecular Weight:
53594.49 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
13. Gamma-aminobutyric acid receptor subunit gamma-2
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
Gene Name:
GABRG2
Uniprot ID:
P18507
Molecular Weight:
54161.78 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
14. Gamma-aminobutyric acid receptor subunit gamma-3
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRG3
Uniprot ID:
Q99928
Molecular Weight:
54288.16 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
15. Gamma-aminobutyric acid receptor subunit pi
General Function:
Gaba-a receptor activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. In the uterus, the function of the receptor appears to be related to tissue contractility. The binding of this pI subunit with other GABA(A) receptor subunits alters the sensitivity of recombinant receptors to modulatory agents such as pregnanolone.
Gene Name:
GABRP
Uniprot ID:
O00591
Molecular Weight:
50639.735 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
16. Gamma-aminobutyric acid receptor subunit rho-1
General Function:
Gaba-a receptor activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-1 GABA receptor could play a role in retinal neurotransmission.
Gene Name:
GABRR1
Uniprot ID:
P24046
Molecular Weight:
55882.91 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
17. Gamma-aminobutyric acid receptor subunit rho-2
General Function:
Gaba-a receptor activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-2 GABA receptor could play a role in retinal neurotransmission.
Gene Name:
GABRR2
Uniprot ID:
P28476
Molecular Weight:
54150.41 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
18. Gamma-aminobutyric acid receptor subunit rho-3
General Function:
Gaba-a receptor activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRR3
Uniprot ID:
A8MPY1
Molecular Weight:
54271.1 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]
Target Details
19. Gamma-aminobutyric acid receptor subunit theta
General Function:
Transmembrane signaling receptor activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRQ
Uniprot ID:
Q9UN88
Molecular Weight:
72020.875 Da
References
  1. Ikeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T: Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons. Br J Pharmacol. 1999 Aug;127(7):1567-76. [10455311 ]