Tutin (CED0009410)

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 an exogenous organic compound with the formula C15H18O6 and an average molecular weight of 294.30 g/mol. It exists as a solid at room temperature. Tutin belongs to the gamma butyrolactones, a subclass of lactones within the organic compounds. The compound is a potent antagonist of the glycine receptor, with four recorded protein targets: glycine receptor subunit alpha-1 (GLRA1), glycine receptor subunit alpha-2 (GLRA2), glycine receptor subunit alpha-3 (GLRA3), and glycine receptor subunit beta (GLRB). Tutin is found in or released from 30 recorded sources across various categories. In the realm of electrical and electronic equipment, it is associated with antennas, coils, adjustable resistors, auxiliary devices, cores yokes or armatures, and 12 other sources. Within building and construction, it is linked to tents or canopies, ladders, fencing, stairs and ramps, and roofs. It is also found in household items such as badges, and in household cleaning and consumer products including soap dispensers, cigar cigarettes, tobacco product moisture control, pipe accessories, and other smoking requisites. Additionally, it is found in food, food processing and cookware, specifically in the processing of meats and fish.

Contaminant Type

Ester
Ether
Human Neurotoxin
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

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	Yes	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	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0090000000-c09eb472d880dd17b91c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-054k-0090000000-b4e51b46c4081fc8cb43	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-2590000000-76e558f6db835c0e279a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-06a636e21bf465a24370	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002g-0090000000-fcf38ecaf9a001c9a6a8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4j-3390000000-de3b7084c66a60291097	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Tutin is a potent antagonist of the glycine receptor. (1)

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

Not Available

Symptoms

Tutin has powerful convulsant effects. (1)

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
46.0	Log mg/kg	[30:82]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
496	Fencing	Building & Construction	Not Available
498	Ladders	Building & Construction	Not Available
499	Roofs	Building & Construction	Not Available
500	Stairs And Ramps	Building & Construction	Not Available
503	Tents Or Canopies	Building & Construction	Not Available
504	Adjustable Resistors	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
507	Auxiliary Devices	Electrical & Electronic Equipment	Not Available
508	Coils	Electrical & Electronic Equipment	Not Available
513	Cores Yokes Or Armatures	Electrical & Electronic Equipment	Not Available
515	Discharge Tubes With Liquid Pool Cathodes	Electrical & Electronic Equipment	Not Available
516	Electric Hearing Aids	Electrical & Electronic Equipment	Not Available
520	Emergency Protective Devices	Electrical & Electronic Equipment	Not Available
523	Gas Filled Discharge Tubes With Solid Cathode	Electrical & Electronic Equipment	Not Available
525	Line Transmission Systems	Electrical & Electronic Equipment	Not Available
527	Magnets	Electrical & Electronic Equipment	Not Available
529	Power Cables	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
531	Relays	Electrical & Electronic Equipment	Not Available
534	Still Video Cameras	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
551	Processing Fish	Food, food processing & cookware	Not Available
552	Processing Meats	Food, food processing & cookware	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
562	Pipe Accessories	Household cleaning & consumer products	Not Available
564	Soap Dispensers	Household cleaning & consumer products	Not Available
568	Tobacco Product Moisture Control	Household cleaning & consumer products	Not Available
570	Badges	Household items	Not Available
578	Making Cigars	Industrial manufacturing & chemical processing	Not Available
579	Manufacture Of Iron Or Steel	Industrial manufacturing & chemical processing	Not Available
592	Marine Propulsion Or Steering	Marine, shipping & aquaculture	Not Available
620	Card Games	Recreation & sports surfaces	Not Available
622	Game Accessories	Recreation & sports surfaces	Not Available
628	See Saws	Recreation & sports surfaces	Not Available
630	Toys	Recreation & sports surfaces	Not Available
634	Buckles	Textiles, leather & furnishings	Not Available
635	Buttons	Textiles, leather & furnishings	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
652	Ropes	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Glycine receptor subunit alpha-2	P22771	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	Serine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoform	Q76MZ3	Mus musculus	Predicted (SEA)	1.40129
Click to view 3D structure	NACHT, LRR and PYD domains-containing protein 3	Q96P20	Humans	Predicted (SEA)	2238.79
Click to view 3D structure	Glycine receptor subunit alpha-2	P23416	Humans	Predicted (SEA)	2.17978
Click to view 3D structure	Transcriptional activator Myb	P01103	Gallus gallus	Predicted (SEA)	8.40772
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 1	P18031	Humans	Predicted (SEA)	4519.69
Click to view 3D structure	Fumarate reductase	F1KRD8	Ascaris suum	Predicted (SEA)	1.01204
Click to view 3D structure	Adenylate cyclase type 1	P19754	Bos taurus	Predicted (SEA)	18.7617
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-4	P28471	Rattus norvegicus	Predicted (SEA)	22.2649
Click to view 3D structure	Asialoglycoprotein receptor 1	P07306	Humans	Predicted (SEA)	24.6004
Click to view 3D structure	Tegument protein VP16	P06492	Herpes simplex virus (type 1 / strain 17)	Predicted (SEA)	5405.69
Click to view 3D structure	3-oxoacyl-[acyl-carrier-protein] synthase 2	P9WQD7	Mycobacterium tuberculosis	Predicted (SEA)	4.35956
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	4131.46
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	6179.13
Click to view 3D structure	Replicase polyprotein 1ab	P0DTD1	SARS-CoV-2	Predicted (SEA)	6840.07
Click to view 3D structure	Bile acid receptor	Q96RI1	Humans	Predicted (SEA)	5835.73
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	645.681
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	2461.98
Click to view 3D structure	Tubulin--tyrosine ligase	Q8NG68	Humans	Predicted (SEA)	20.9414
Click to view 3D structure	Phospholipase A2 alpha	P00623	Crotalus adamanteus	Predicted (SEA)	13.6236
Click to view 3D structure	Ubiquitin-conjugating enzyme E2 D3	P61077	Humans	Predicted (SEA)	161.148
Click to view 3D structure	Serine-threonine protein phosphatase 2A regulatory subunit	Q8AWE3	Gallus gallus	Predicted (SEA)	131.02
Click to view 3D structure	Transcription factor p65	Q04206	Humans	Predicted (SEA)	1433.9
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	271.071
Click to view 3D structure	NACHT, LRR and PYD domains-containing protein 3	Q8R4B8	Mus musculus	Predicted (SEA)	3316.38
Click to view 3D structure	Glycine receptor subunit alpha-1	P23415	Humans	Known	Tutin is a potent antagonist of the glycine receptor. (L1250)
Click to view 3D structure	Glycine receptor subunit alpha-2	P23416	Humans	Known	Tutin is a potent antagonist of the glycine receptor. (L1250)
Click to view 3D structure	Glycine receptor subunit alpha-3	O75311	Humans	Known	Tutin is a potent antagonist of the glycine receptor. (L1250)
Click to view 3D structure	Glycine receptor subunit beta	P48167	Humans	Known	Tutin is a potent antagonist of the glycine receptor. (L1250)