ContaminantDB: Tutin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-07-23 18:26:11 UTC

Update Date

2026-04-05 15:21:40 UTC

Accession Number

CHEM002425

Identification

Common Name

Tutin

Class

Small Molecule

Description

Tutin is a plant toxin found in the tutu plant (genus Coriaria). It has powerful convulsant effects. (1)

Contaminant Sources

T3DB toxins

Contaminant Type

Ester
Ether
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Coriaria lactone	MeSH
2a,3a-Epoxy-3a,4a,5,6,7,7a-hexahydro-3a alpha,6 beta,7 beta-trihydroxy-5 alpha-isopropyl-7a alpha- methylspiro(indan-1,2'-oxirane) gamma-lactone	MeSH

Chemical Formula

C₁₅H₁₈O₆

Average Molecular Mass

294.300 g/mol

Monoisotopic Mass

294.110 g/mol

CAS Registry Number

2571-22-4

IUPAC Name

2',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 Name

2',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

SMILES

CC(=C)C1C2OC(=O)C1C1(O)C3OC3C3(CO3)C1(C)C2O

InChI Identifier

InChI=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 Key

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma 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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

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	19 mg/mL at 10°C [BEILSTEIN]

Predicted Properties

Property	Value	Source
Water Solubility	38.7 g/L	ALOGPS
logP	-0.11	ALOGPS
logP	-0.66	ChemAxon
logS	-0.88	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.47 m³·mol⁻¹	ChemAxon
Polarizability	28.23 Å³	ChemAxon
Number of Rings	5	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	splash10-0002-0090000000-c09eb472d880dd17b91c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-054k-0090000000-b4e51b46c4081fc8cb43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-2590000000-76e558f6db835c0e279a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-06a636e21bf465a24370	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002g-0090000000-fcf38ecaf9a001c9a6a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4j-3390000000-de3b7084c66a60291097	Spectrum

Toxicity Profile

Route of Exposure

Oral (ingestion) (2) ; dermal (2)

Mechanism of Toxicity

Tutin is a potent antagonist of the glycine receptor. (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

Tutin is a plant toxin found in the tutu plant (genus Coriaria). (1)

Minimum Risk Level

Not Available

Health Effects

Tutin has powerful convulsant effects. (1)

Symptoms

Tutin has powerful convulsant effects. (1)

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

Tutin

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

122160

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

Tutin (CHEM002425)

Structure for CHEM002425: Tutin