ChemFOnt: Showing chemical card for Toxin T2 tetrol (CFc000017146)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:07:00 UTC

Chemfont ID

CFc000017146

Molecule Identification

Common Name

Toxin T2 tetrol

Definition

T-2 Tetraol is a type-A trichothecene mycotoxin produced by different Fusarium species, including F. soprotrichioides, F. poae, and F. acuinatum that contaminate feedstuffs and cereal grains (PMID: 11843402 , 31683661 ). T-2 Tetraol shows the highest toxicity in animals compared to other trichothecenes. It contains a tetracyclic sesquiterpenoid 12,13-epoxytrichothec-9-ene ring which is responsible for the high toxicological activity (PMID: 12749813 ). In T-2 Tetraol, a carbonyl group at the C-8 position is substituted by an ester. T-2 Tetraol is resistant to light and temperature, but sensitive to strong acid or alkaline conditions. Some coexisting bacteria or fungi can detoxify T-2 Tetraol by altering its structure. It is associated with a wide range of effects in animals including weight loss, diarrhea, lethargy, low plasma glucose, decreases in blood cell and leukocyte count. damage to cartilaginous tissues, and induction of apoptosis (PMID: 21417259 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
12,13-Epoxy-trichothec-9-ene-3alpha,4beta,8alpha,15-tetrol	HMDB
T 2 Toxin tetraol	HMDB
T-2 Tetraol	HMDB
T-2 Tetraol toxin	HMDB
T-2 Tetrol	HMDB
T2 Tetrol	HMDB
Toxin T 2 tetraol	HMDB
Toxin T 4	HMDB

Chemical Formula

C₁₅H₂₂O₆

Average Molecular Weight

298.3316

Monoisotopic Molecular Weight

298.141638436

IUPAC Name

2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-ene-4',10',11'-triol

Traditional Name

2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-ene-4',10',11'-triol

CAS Registry Number

34114-99-3

SMILES

CC1=CC2OC3C(O)C(O)C(C)(C33CO3)C2(CO)CC1O

InChI Identifier

InChI=1S/C15H22O6/c1-7-3-9-14(5-16,4-8(7)17)13(2)11(19)10(18)12(21-9)15(13)6-20-15/h3,8-12,16-19H,4-6H2,1-2H3

InChI Key

ZAXZBJSXSOISTF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

Trichothecene skeleton
Oxepane
Oxane
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Health effect

Observation

Circulatory system disorder

Vascular disorder

Hypotension (HMDB: HMDB0036159)

Blood and lymphatic system disorder

Shock (HMDB: HMDB0036159)

Disposition

Biological location

Cellular substructure

Route of exposure

Parenteral

Dermal (HMDB: HMDB0036159)
Inhalation (HMDB: HMDB0036159)

Enteral

Ingestion (HMDB: HMDB0036159)

Source

Endogenous

Endogenous (HMDB: HMDB0036159)

Animal

Animal (HMDB: HMDB0036159)

Exogenous

Food

Food (HMDB: HMDB0036159)

Exogenous (HMDB: HMDB0036159)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036159)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036159)

Lipid metabolism pathway (HMDB: HMDB0036159)

Cellular process

Cell signaling (HMDB: HMDB0036159)

Biochemical process

Lipid transport (HMDB: HMDB0036159)

Role

Biological role

Energy source (HMDB: HMDB0036159)

Environmental role

Environmental contaminant (HMDB: HMDB0036159)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	63.7 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.7	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Acidic)	12.96	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	102.68 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.31 m³·mol⁻¹	ChemAxon
Polarizability	29.83 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036159

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015012

KNApSAcK ID

C00012637

Chemspider ID

521016

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

599328

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Toxin T2 tetrol (CFc000017146)

MOL for CFc000017146 (Toxin T2 tetrol)

3D MOL for CFc000017146 (Toxin T2 tetrol)

3D SDF for CFc000017146 (Toxin T2 tetrol)

3D-SDF for CFc000017146 (Toxin T2 tetrol)

PDB for CFc000017146 (Toxin T2 tetrol)

3D PDB for CFc000017146 (Toxin T2 tetrol)

SMILES for CFc000017146 (Toxin T2 tetrol)

INCHI for CFc000017146 (Toxin T2 tetrol)

Structure for CFc000017146 (Toxin T2 tetrol)

3D Structure for CFc000017146 (Toxin T2 tetrol)