Tutin

Basic Info

Common NameTutin(F04802)
2D Structure
Description

Tutin is a plant toxin found in the tutu plant (genus Coriaria). It has powerful convulsant effects. (L1250)

FRCD IDF04802
CAS Number2571-22-4
PubChem CID75729
FormulaC15H18O6
IUPAC Name

None

InChI Key

CCAZWUJBLXKBAY-ULZPOIKGSA-N

InChI

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/t6-,7+,8+,9+,10+,11-,13-,14+,15-/m0/s1

Canonical SMILES

CC(=C)C1C2C(C3(C4(CO4)C5C(C3(C1C(=O)O2)O)O5)C)O

Isomeric SMILES

CC(=C)[C@@H]1[C@@H]2[C@H]([C@]3([C@@]4(CO4)[C@H]5[C@@H]([C@]3([C@H]1C(=O)O2)O)O5)C)O

Synonyms
        
            Toot poison
        
            (1aS-(1aalpha,1bbeta,2beta,5beta,6alpha,6abeta,7beta,7aalpha,8S*))-Hexahydro-1b,6-dihydroxy-6a-methyl-8-(1-methylethenyl)spiro(2,5-methano-7H-oxireno(3,4)cyclopent(1,2-d)oxepin-7,2'-oxiran)-3(2alpha H)-one
        
            Tutin
        
            Tutine
        
            Tutu
        
            2571-22-4
        
            UNII-B69P754702
        
            CHEBI:9783
        
            B69P754702
        
            Spiro(2,5-methano-7H-oxireno(3,4)cyclopent(1,2-d)oxepin-7,2'-oxiran)-3(2ah)-one, 1a-beta,1b,5a,6,6a,7a-beta-hexahydro-1b-alpha,6-beta-dihydroxy-8a-isopropenyl-6a-alpha-methyl-
Classifies
                

                  
                    Plant Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassLactones
SubclassGamma butyrolactones
Intermediate Tree NodesNot available
Direct ParentGamma butyrolactones
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsOxepane - 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
DescriptionThis compound belongs to the class of organic compounds known as gamma butyrolactones. These 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.

Properties

Property NameProperty Value
Molecular Weight294.303
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count1
Complexity603
Monoisotopic Mass294.11
Exact Mass294.11
XLogP-0.5
Formal Charge0
Heavy Atom Count21
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.6154
Human Intestinal AbsorptionHIA+0.7661
Caco-2 PermeabilityCaco2-0.6102
P-glycoprotein SubstrateSubstrate0.7625
P-glycoprotein InhibitorNon-inhibitor0.7333
Non-inhibitor0.9784
Renal Organic Cation TransporterNon-inhibitor0.7864
Distribution
Subcellular localizationMitochondria0.6116
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8053
CYP450 2D6 SubstrateNon-substrate0.8576
CYP450 3A4 SubstrateSubstrate0.6252
CYP450 1A2 InhibitorNon-inhibitor0.8026
CYP450 2C9 InhibitorNon-inhibitor0.8534
CYP450 2D6 InhibitorNon-inhibitor0.8974
CYP450 2C19 InhibitorNon-inhibitor0.7948
CYP450 3A4 InhibitorNon-inhibitor0.7029
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6464
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9960
Non-inhibitor0.8724
AMES ToxicityNon AMES toxic0.5799
CarcinogensNon-carcinogens0.9537
Fish ToxicityHigh FHMT0.9384
Tetrahymena Pyriformis ToxicityHigh TPT0.6557
Honey Bee ToxicityHigh HBT0.8451
BiodegradationNot ready biodegradable0.9950
Acute Oral ToxicityI0.4498
Carcinogenicity (Three-class)Non-required0.6547
Model Value Unit
Absorption
Aqueous solubility-2.9005LogS
Caco-2 Permeability0.9066LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.5005LD50, mol/kg
Fish Toxicity0.2131pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3404pIGC50, ug/L

References

TitleJournalDatePubmed ID
Glycosides of the Neurotoxin Tutin in Toxic Honeys Are from Coriaria arborea Phloem Sap, Not Insect Metabolism.J Nat Prod2018 Apr 2729504746
Poisoning due to tutin in honey-a report of an outbreak in New Zealand.N Z Med J2018 Apr 1329649198
Sweet Poisons: Honeys Contaminated with Glycosides of the Neurotoxin Tutin.J Nat Prod2015 Jun 2625993882
Tutu toxicity: three case reports of Coriaria arborea ingestion, review of literature and recommendations for management.N Z Med J2013 Mar 123474518

Targets

Target Details

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
Mechanism of Action:
Tutin is a potent antagonist of the glycine receptor.
References
  1. Wikipedia. Tutin. Last Updated 23 May 2009. : http://en.wikipedia.org/wiki/Tutin
Target Details

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
Mechanism of Action:
Tutin is a potent antagonist of the glycine receptor.
References
  1. Wikipedia. Tutin. Last Updated 23 May 2009. : http://en.wikipedia.org/wiki/Tutin
Target Details

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
Mechanism of Action:
Tutin is a potent antagonist of the glycine receptor.
References
  1. Wikipedia. Tutin. Last Updated 23 May 2009. : http://en.wikipedia.org/wiki/Tutin
Target Details

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
Mechanism of Action:
Tutin is a potent antagonist of the glycine receptor.
References
  1. Wikipedia. Tutin. Last Updated 23 May 2009. : http://en.wikipedia.org/wiki/Tutin
Target Details

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
Mechanism of Action:
Tutin is a potent antagonist of the glycine receptor.
References
  1. Wikipedia. Tutin. Last Updated 23 May 2009. : http://en.wikipedia.org/wiki/Tutin