Tutin (T3D3089)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (5)XML
Targets (5)
Record Information
Version2.0
Creation Date2009-07-23 18:26:11 UTC
Update Date2014-12-24 20:25:58 UTC
Accession NumberT3D3089
Identification
Common NameTutin
ClassSmall Molecule
DescriptionTutin is a plant toxin found in the tutu plant (genus Coriaria). It has powerful convulsant effects. (1)
Compound Type
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Toot poison
Tutine
TUTU
Chemical FormulaC15H18O6
Average Molecular Mass294.300 g/mol
Monoisotopic Mass294.110 g/mol
CAS Registry Number2571-22-4
IUPAC Name2',8'-dihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-11'-one
Traditional Name2',8'-dihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-11'-one
SMILESCC(=C)C1C2OC(=O)C1C1(O)C3OC3C3(CO3)C1(C)C2O
InChI IdentifierInChI=1S/C15H18O6/c1-5(2)6-7-12(17)20-8(6)9(16)13(3)14(4-19-14)10-11(21-10)15(7,13)18/h6-11,16,18H,1,4H2,2-3H3
InChI KeyInChIKey=CCAZWUJBLXKBAY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Oxepane
  • Gamma butyrolactone
  • Oxane
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
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
Solubility19 mg/mL at 10°C [BEILSTEIN]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility38.7 g/LALOGPS
logP-0.11ALOGPS
logP-0.66ChemAxon
logS-0.88ALOGPS
pKa (Strongest Acidic)12.69ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.82 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.47 m³·mol⁻¹ChemAxon
Polarizability28.23 ųChemAxon
Number of Rings5ChemAxon
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, Negativesplash10-0006-0090000000-06a636e21bf465a243702016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002g-0090000000-fcf38ecaf9a001c9a6a82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-3390000000-de3b7084c66a602910972016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-c09eb472d880dd17b91c2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054k-0090000000-b4e51b46c4081fc8cb432016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-2590000000-76e558f6db835c0e279a2016-08-01View Spectrum
Toxicity Profile
Route of ExposureOral (ingestion) (2) ; dermal (2)
Mechanism of ToxicityTutin is a potent antagonist of the glycine receptor. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesTutin is a plant toxin found in the tutu plant (genus Coriaria). (1)
Minimum Risk LevelNot Available
Health EffectsTutin has powerful convulsant effects. (1)
SymptomsTutin has powerful convulsant effects. (1)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID75729
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC09570
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDTutin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Wikipedia. Tutin. Last Updated 23 May 2009. [Link]
  2. Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Glycine receptor subunit alpha-1
General Function:
Transmitter-gated ion channel activity
Specific Function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name:
GLRA1
Uniprot ID:
P23415
Molecular Weight:
52623.35 Da
References
  1. Wikipedia. Tutin. Last Updated 23 May 2009. [Link]
Target Details
2. Glycine receptor subunit alpha-2
General Function:
Transmitter-gated ion channel activity
Specific Function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name:
GLRA2
Uniprot ID:
P23416
Molecular Weight:
52001.585 Da
References
  1. Wikipedia. Tutin. Last Updated 23 May 2009. [Link]
Target Details
3. Glycine receptor subunit alpha-3
General Function:
Transmitter-gated ion channel activity
Specific Function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name:
GLRA3
Uniprot ID:
O75311
Molecular Weight:
53799.775 Da
References
  1. Wikipedia. Tutin. Last Updated 23 May 2009. [Link]
Target Details
4. Glycine receptor subunit alpha-4
General Function:
Transmitter-gated ion channel activity
Specific Function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name:
GLRA4
Uniprot ID:
Q5JXX5
Molecular Weight:
47727.92 Da
References
  1. Wikipedia. Tutin. Last Updated 23 May 2009. [Link]
Target Details
5. Glycine receptor subunit beta
General Function:
Glycine binding
Specific Function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name:
GLRB
Uniprot ID:
P48167
Molecular Weight:
56121.62 Da
References
  1. Wikipedia. Tutin. Last Updated 23 May 2009. [Link]